Friday, May 29, 2009

An Open Letter to (that minx) Rashida Jones

Rashish -- we have a problem sister friend --

You seem to be a little bit confused about what I like to call "the way things work up in this piece."

See you -- the bangin', bi-racial daughter of a famous black R&B musician are supposed to engage in some variation of the following: be hot mess, get knocked up by someone with tatoos in the dumbest places, disappear for a few years then come back with a KMart kids clothing line.

You are not supposed to date the intellectual savior of Obamanation. John Favreau is ours.

You get the Hollywood people. The John Krasz-on-the-Office's, the Used-to-be-Zach-Slater's. You understand them and their overwhelming vanity. They understand you and your face. The rest of us just can't leave work every other week to go lounge around in St. Tropez. Also we don't have publicists who call them and say, "Hi Guy-from-that-show-Castle (in loooove...), Jessie would love to grab a drink with you next week."

And so the world goes round with you dating its celebrities and us dating it's really smart people with 9-5 jobs.

I know John Favreau is among the greatest brains of our generation. I know he is the kind of writer that comes around once in a metaphor stronger than blue moon. I also know he's done all that at the really-quite-perfect-for-me age of 27.

That's why I studied my ass off through high school, got into a top notch college, and honed all sorts of necessary skills so I could eventually end up with someone like him (if not actually him).

What have you done in the past -- oh -- ever -- to deserve to be on the right arm of this perfect man. Appeared in The Office?! Or that movie where Jason Segal gets naked? You appear on movies where non-models get naked for no reason and then go date the guy who wrote the innagural address. How daaare you.

Break up with him. It's only fair. I promise you'll have no trouble finding a replacement. Then the rest of us can go on believing that if we could just meet him in a bar somewhere and regale him with our memorized recount of all the state senators (alphabetical by state) he'll be ours.

Also -- who does you hair? So cute.


Wednesday, May 27, 2009

How to make other people make you look good

Back to this issue of the "Generic Me" that John brought up last Friday.

There is -- like it or probably not -- a one to two sentence description our friends use to pitch us to people who may want to date us (that's after they get through the physical description).
  • "Oh you want to know about Amber? She's cute, brown hair, pretty tall and thin -- and she's the assistant to a movie producer. Hates the job but meets awesome people." Hello, Amber.
  • "Yeah, sure I'll introduce you to John, he's great -- ibanker by day but also does all this cute volunteer stuff." John: defined..and redeemed.

  • "Mmm Rebecca? Well, cute girl, but she's currently unemployed and generally dates assholes." Sucks for you Rebecca.
This is not fair but neither is the fact that gays can't marry (Damn you CA!), so we'll just have to learn to deal.

I'm no stranger to the effects of the "Name : Description" game:
  • You know my friend Jessie -- the one who writes that blog all about dating and relationships? Um...yeah, sometimes she writes about people she dates, but don't worry -- she only does it if they're real assholes -- usually.
Naturally I'd prefer something along the lines of:

  • You should meet my friend Jessie. She looks a lot like Minnie Driver, loves to walk around the city, and has shoes for every occasion.
...but that's two truth's and a lie...

And so since we can't hide behind our one-sentence selves we must "campaign" to friends, family, co-workers, and laundry ladies to encourage them to pitch our best selves.

But Jessie! -- you say to whatever you read this on -- that's deceitful...putting on airs...manipulating the truth!

Relax. It's just guiding the outlets broadcasting your specific message (that being who you are in two sentences or less) to achieve your desired response. Lost? Good.

I recommend the following methods to inspire others to make you look good when they talk about you:

  • Drop subtle hints by describing yourself like you want them to describe you. Example. You: "So Jill told Adam that I was an energetic media person who loves good food and online news portals. Isn't that exactly the way you'd describe me?! I just thought it was so perfect and, as such, really liked Jill more than I ever have before so I gave her a nice gift." Adapt as necessary.

  • Ask directly under the cover of a personal image overhaul project. You: "I know this is going to sound weird, but I'm really trying to focus on volunteer work more, so I think it would be helpful if you always describe me to people -- or guys -- or, you know, whoever -- with a focus on that community involvement angle because it'll help put that idea of me into the universe more. Make sense?" If they challenge this tell them it is a part of "The Secret" and that if they don't do it they won't ever get anything they want in life.

  • Barter -- very hot right now. Make arrangements with key contacts that you will always describe them in a given light if they return the favor. I, for example, have expressed to certain friends that I will never mention how they act when drunk if they don't immediately reveal that I judge all male dating behavior via an online column.

  • Be better. It could be that people give you bad review because you're not (currently) that great. If you're a real asshole or a generally lame person people will probably share that with their friends who (for some reason) want to date you so you don't dick those friends over. Maybe if you try to be a better person and do some great (good even..) things your friends and colleagues will be able to talk about those things to others. Simple logic here.
Good luck out there. And if it goes particularly well please report that this single writer named Jessie who appreciates both college sports and art museums helped you out.

Tuesday, May 26, 2009

Do we expect too much out of marriage?

I was chatting with friends this past weekend when the relationship issues of a couple not present came up and under judgement. This tends to happen when groups of people I know get together and drink alcohol.

Someone was saying they wished ____________ and ___________, as two successful, attractive, youthful people had more obvious love and romance in their life (sex). That it’s a shame they don’t love each other like they should and deserve to be loved. Someone else said that not every relationship is so overtly filled with passion/romance/sex all the time. That they may actually love each other more than some people who have overtly passionate relationships. That, after a certain length of time, the sex/passion gets detached from the bond/commitment. You don’t need one to have the other. It ebbs and flows.

We went back and forth like this for awhile because we were drunk and one of us is in law school – but the bottom line became that the person arguing this couple’s relationship was unfortunate because of its lack of sex and passion was expecting too much out of committed, romantic (read: married) love. That his position was obviously young and inherently American.

Do American 25-year-olds (a mental age that can sit anywhere from 20 to 35…) expect too much from romantic love -- and more specifically marriage?

Well - step one - what do "we" expect?

Paraphrasing from our convo -- that we will meet and fall in love with a person who inspires in us the best version of our (already complete) selves and then jointly commit to a life-long partnership supporting our mutual goals while maintaining a care for our sexual needs -- in sickness and health..and with kids..and if one of us loses a job..and if neither of us “make it” where we thought we would..and with the in-laws…

Ring a tune?

I think some of us – wisely or not – expect different than that. Not more (“and that we’ll never question our decision to be with that person ever”) or less (“that we may choose someone because of lifestyle plus love, not just straight head-over-heels-ness”) but the majority of hoping-to-be-marrieds are after the whole package. No one sets out to be a C-list celebrity.

But to say that’s “too much” is to suggest it’s not possible – or highly unlikely. Managing our expectations about committed bliss after the 5, 10, 20 years is the smarter bet. To go in expecting challenges and unhappiness and maybe years without sex because -- well -- Icarus got burned.

I was drunk, but I think the person arguing for the flight to the sun was saying that the less you expect the easier you slip. Take a pass/fail class and you’ll likely damn-near fail. Go in wanting just enough out of your life-long partner and you’ll get that if not slightly less.

I don’t know the answer, but I’m not sure it would even affect the expectation. We know that 50+% of marriages end in divorce. We know research shows some of the happiest and most stable couples come from arranged marriages in places like India. If there was a Cool-Aid to drink it might actually support never getting married at all.

And yet we end relationships with loving, stable med students because “it just wasn’t there.”

Is that American? Is it 25-year-old? Is it wrong or is it right?

In 40 years who will end up happier? My friend who argued that you can consistently have it all or the one with a less rose-colored approach? And how much will that happiness have to do with their position going in?

Friday, May 22, 2009

John's response to my post on his new-found balls -- "on" in this case meaning "about"

John's response to Wednesday's post about him is as follows:

I enjoyed your take on our conversation, save the cringe inducing, Carrie Bradshaw voiceoveresque quote about rose petals. Let me respond with my take on things.

First, there are “dude cycles.” Any twenty something guy will go in cycles as to what he wants from women. Mine, and I would guess many other guys’, goes like this….

I will find myself in a serious relationship. The girl will be attractive, fun, nice, etc. But she won’t be “I don’t wanna ever have sex with another girl” attractive, nice, etc. At some point, usually about 6-8 months in, I will have to come to terms with the questions of where is this going, could I marry this girl, is she a “one.” And ultimately I will break things off, knowing I am not ready to get THAT serious. Then I will spend the next 6-8 months doing some variety of hitting on random girls, trying to hook up with girls I had been thinking about hooking up with while with said girlfriend, succeeding at times, being rejected at others, and generally living the single life.

Then at some point something clicks, and I will miss the whole splitting a bottle of wine (read: 3), watching a movie, nice dinner, fill in the blank fun thing that couples do together. Also, at this point I usually have remembered that random hook-ups with Anne Hathoway lookalikes are probably not gonna happen. This is basically how things have gone for the last four or so years of my life.

Second, and this goes more as to why I have become a bit more balsy (some may say sketchy) about pursuing women, is what Generic Me is.

Generic Me is how someone would describe me in one sentence to a girl. Four years ago, Generic John was pretty similar to the other 1,000 senior dudes at BC. I really had nothing particularly out of the ordinary going for me. That’s changed a bit now for two reasons.

First, the girls I pursue now are not in college and therefor don’t have tons of men all over them all the time. They are looking for the things mid twenty year olds are looking for, not 21 year olds.

Second, I’ve had a mildly successful four years. So I could imagine someone saying to a girl “I know this guy John who thinks you’re cute. He is gonna be a doctor soon, seems friendly and normal, and wants to get your number to take you out for a drink.” I think at least a decent number of girls would be receptive to that.

So Jessie, this brings us back to your question about if things had changed.

I don’t think anything out of the usual really has. I am not suddenly looking for a wife. A reader left a comment where she speculates that for guys its more about being ready than finding the one. I have always wondered this myself and I really don’t know the answer. But I certainly don’t look back at any past girlfriend and think “If I had met them now I would marry them.” So maybe it’s just a matter of keeping on lookin’.

Ed note: on Monday we discuss this whole Generic Me issue. Thank you John -- that's three posts for you in two weeks. Mike is going to be SO mad...

Wednesday, May 20, 2009

When it becomes riskier to NOT go after the girl

My friend John recently confirmed my long-held belief that when a guy's ready, nothing will stop him from pursuing a girl.

John's a catch.  Musically-talented, Boston College-educated, 4th year med student with a great sense of humor and a group of guy friends that people write tv shows and movies about.  As such he has dated his share of quality ladies -- some for legitimate amounts of time.  But when each ended John would admit that he just wasn't ready to get in that kind of committed relationship. 

"Then you must not like her that much..." I'd argue.  "I don't know," he'd say, "I'm just not ready yet."

Classic guy line.

But suddenly this past weekend over one of our tri-monthly check-in (if that means every 3rd month) he sang a very different tune.

"Jessie," he said, "I think I'm at that point where I could really date a girl for awhile now -- really be in a relationship."  And then he shared the following story which I hope I'm not butchering...

John is a runner so he went into a running store to buy whatever it is they sell there.  At said store was a shop girl girl he found instantly attractive. She may or may not have been related to the store owner -- I can't remember.  Given the logistics of his shopping transaction there wasn't occasion to ask for her number (note that he never mentioned just leaving his behind.  He wanted hers), so he went back a few days later to see if she was there intending to fake buy, I don't know, probably socks. 

Sadly no dice, but John wasn't about to let this die.  He went to a doctor who works in his hospital and also frequents this local running shop and told the doctor he needed to contact this girl.  The doctor referred him to a family friend of the running store owner who through two additional steps that were a bit unclear (John mumbles sometimes) procured the girl's cell phone number.  John called it the day he got it and left a message for the girl.  

This specific story is open-ended because shop girl's on vacation for the rest of this week, but that's not the point. 

The point is that John finally arrived at a place where he viewed it as riskier to not go to those lengths to get the girl.  "I'm just at this point where I don't care anymore," he told me, "I'm going to pursue it if I think there's something there."  Is it 1 parts balls, 1 part logic and the rest what my Mom would call, "a feeling?" I don't know.  I don't know if John really knows. 

There's this Anais Nin quote I've always really loved that goes, "And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom."

That is hoakey and John will roll his eyes when he reads it, but that's exactly his situation."  It wasn't about this specific girl -- he 100% doesn't know her.  It's about him being in a place where any girl of remotely strong interest is worth pursuing because he's ready to find someone great.  Maybe she'll blow him off.  Maybe she'll be the greatest girl he's ever met.  The point is that he'll now take the embarrassment of the blow off in exchange for her maybe being the greatest.  

The question -- per usual -- is why.  What changed in his outlook?  When did it start? And will he revert back if a few pursuits don't work out?

We'll see what he has to say after I tell him I wrote this post about now need answers.  Until then -- what's your take? 

Monday, May 18, 2009

The difference between college and everything after

As you read this my (oldest) little sister is graduating from college --- the Boston College, specifically -- the same college where I graduated four years ago this very weekend.

As of today I have been out of college for exactly as long as I was in. I'm already prone to over dramatics -- this is like being a binge eater at a buffet.   

Since the end of my own four (A-game!!) years I've had hers to (delicately...?) micro-manage.  I was instituted as den mother to her girl and guy group answering IMs of, "should I overload this semester?!" (not unless you absolutely have to) and, "it is really that important to go abroad??" (yes, times 2) and supplying hand-me-downs in the form of theme party gold (The Franzia Formal, Liquor Treat) and other tricks of the trade (bring nips, buy sodas, save hundreds).

For the past few months their "teach us!" questions have shifted to frantic gchats begging for some assurance that it won't all be hell the minute they leave the comforts of their Mod (If you know what it is, you know what it is.  If you don't -- don't worry about it).


My real answers: Yes. Maybe. No. If you're brave. Probably, but don't.  And yes, tons of them -- but I'm selective about how honestly I answer -- they put blinders on wild race horses for a reason.

There are one million differences between college and everything after, and if I start to name them all you, and I, and my poor hungover little sister will go fetal position until we promise to somehow get her into grad school this Fall.    

To me though, aside from the significant of Microsoft Excel skills and fact that you have to pay for your own dental work -- the most important difference between college and actual life is that intangible element of community.  

When you move into your very first real-person apartment there will not be a construction paper flip-flop on the door with your name and the name of your roommate on it.   On your first day of work you will absolutely not play Never Have I Ever or some equally ridiculous ice-breaker.  If you meet someone out at a party you can't just assume you'll run into them in the dining hall the next day.  You have to get their contact information and then contact them. There will never be an Activities Fair with tables representing every club and team you're strongly encouraged to join.    

It's not that you're alone -- you could, like me, move to a city with four of your five best girl friends (we miss you Liz!!) -- it's just that you're unorganized and no one's going to plan you a Welcome to Real Life! BBQ  to gather you all together.

You have to do it yourself.  

You have to establish gmail chains to keep everyone in touch and you can't be lazy about emailing back. You have to set aside a weekend every year to get everyone together for a reunion.  You have to be friendly and forward and self-starting at your new job so people include you in their plans and make you their friend.  People will make fun of you, but I'd recommend you set up some sort of "Summer Sundays" once a month in a park to get everybody together.  And while there are hundreds of "meet up" groups and political organizations and Zog intramural sports teams to join, but you have to go online and find them. 

I told my sister she couldn't read this today, but if you're equally about to go fetal -- wait -- I'm not finished. 

Yes it is scary.  I know -- it is annoying.  And for me it was very overwhelming and even more depressing.  But after you calm down and (I) stop(pped) crying you realize that it's finally all your own.   

When I was at Boston College I was a Boston College student who'd elected to participate in x,y, and z established campus activities.  I was defined by myself, yes -- but more so my surroundings -- what was available to me.  Everything I now have I mine.  I made it. I chose it.  In some cases I fought for it.  And I 100% paid for it.  

At first that felt like more than I could ever handle.  But after 4 years -- exactly -- it feels really, really good.

Friday, May 15, 2009

Don't send this email(s)

There will (has?) come a time(s) when you will be faced with whether or not to send a follow-up email to a guy/girl you (thought you) hit it off with, subsequently emailed and have since heard nothing from.

Here are your options:

The you-think-this-sounds-totally-reasonable-slash-believable

Subject line: Just wanted to check in

Hey _____________,

Really fun meeting you that other night at _________________. Thought I’d be a little brazen and reach out again just to say I had a really great time with you, so let me know if you want to grab another drink sometime. I know you have my number from that night, but just in case I gave it to you wrong or something – I’m 555-2222.

Hope you’re having a great day!

The angry

Subject line: ???


I’m sure it’s been crazy at work for you, but just wonder if you got my email 1.5 weeks ago and have any interest in the drink we talked about extensively when we met and spent the entire evening together. No worries at all if you’re no longer interested, but could you just drop me a line to let me know so I can confirm in my mind that you’re not an option? You could just say, “Hey, sorry, going to be totally busy over the next few weeks” and I’ll know what that means because everyone knows what that means.


The passive aggressive

Subject line: Hi :)

Hey _______________,

Just checking in to say hi again. Loving the gorgeous weather, right?!

Hope all’s well!

The I'll teach you a lesson

Subject line: Listen...

Okay ___________,

I get that you’re not interested in hanging out again because you haven’t returned my email in close to two weeks. But my thing is, don’t say, “you’re really great, we should get drinks this weekend” if you a. know for a fact that won’t happen or b. think there’s a chance that won’t happen. If you know for a fact please stop talking to me and walk away. If you think there’s a chance say, “give me your number, maybe I’ll call you sometime.” But to say “we should get drinks this weekend” and then not respond to an email for 2 weeks when I know full well you have an iphone is just weird. Don’t do it.

Thank you.

The CW show character

Subject line: No subject

Hey ☺

Super fun getting to know you that night back at Chance’s party. I think I totally dropped you a line afterwards but cannot for the life of me keep things straight these days!! Anyway – drinks! Soon! We’re sooo much fun together, with alcohol.


The Seinfeld

Subject line: So this is crazy...


So, I get this email the other day from this person I’m helping out with a freelance writing assignment gig – not important – but anyway, she’s all, “per my email blah blah” weeks back” and I’m all “wait – I didn’t get an email from her…” So I call the tech guy who looks at my inbox system thing and figures out I’ve been all jammed up weeks and not getting all these random emails! Then I realize I’d tried to send you an email after we met and though, crap! he probably thinks I’m a total asshole! But see it’s the computer that’s the asshole – haha – so here I am again just saying hi…and the night the other week was fun…and we should get a drink sometime, you know, if you’re interested!

Let me know! Oh – and maybe call me or text me too just in case this computer goes haywire on me again! 555-2222.

The Felicity

Subject line: Thoughts

Hey _____________,

So I know I sent you that email awhile back seeing if you were interested in getting a drink, but I’ve been thinking about it and I just think now isn’t the best time for that. I mean, if you were planning on us doing that we still could, but I just wanted to reach out and say not to worry about it because things are just crazy for me right now.

So – yeah – let me know what you were thinking. I’d hate to cancel if you’d made, like, a mental plan or something – but just let me know because no worries if you hadn’t yet.


The business-style

Subject line: FWD: Hey there

Please see the below email dated 1.5 weeks ago.

Let me know status!

The you-think-this-is-sooooo-smooth

Subject line: King of Leon tickets

Hey there,

Hope you’re doing well! I know things are probably crazy for you, but I just wanted to reach out to let you know that I scored two insane tickets to Kings of Leon this Thursday night. I remember that night we hung you were saying you love them, so I wanted to see if you were interested in going. We can just call that our follow-up drinks – haha.

Let me know!

The moral of the story

Other than the angry or the lesson-teaching (which, if you have the balls to send please email me so we can eventually be good friends) these all sound as ridiculous as they are.

If it takes you more than 10 minutes and 2 trusted friends to write an email to someone you like who has blown you off for 1 + weeks, don't write it.      

Wednesday, May 13, 2009

We delete users unfit to date

Maybe you’ve seen these posters around your respective cities?

We delete users unfit to date.

They haunt me. I see one at least once a day in whatever subway station I find myself.

Things I know: is this free online dating site that's giving the other online dating sites you pay for a run for their money. Apparently it was started by some guy as an experiment or business school project or something. He runs it out of his house with like his wife or neighbor or an alternative persona that’s actually just him. He claims that, "its matching algorithms and technology is unmatched, we are the only dating site capable of generating matches in real time. At 26 my algorithms and their results were cited in the Nobel Prize of Mathematics (Fields Medal) paper." I don't really understand that, but it sounds extremely official. Also places like Forbes and BusinessWeek have written about it, so that's something too.

That sums up what I know to date. I have yet to try because I remain scarred from my latest experiment with (no, PartyArty625, I don't want to meet up in Astoria for Indian food because it is in fact NOT the food of my people!). Plus I think this hot pink poster campaign with its "we delete users unfit to date" claim is a crock.

Of course, if I’d figured out how to eliminate people unfit to date I’d have some posters made up too. Or just a really stable relationship and so fuck the posters...

I have taken some significant measures to figure out exactly what this means. After my calls, letters, and emails to the Mr PlentyofFish man (woman?) went unanswered I went to the site and found this code of conduct policy explaining who the site deems unfit to date.

As I suspected -- crock:
  • you will keep all information provided to you through the Service as private and confidential and will not give such information to anyone without the permission of the person who provided it to you;
  • you will not use the Service to engage in any form of harassment or offensive behavior, including but not limited to the posting of communications, pictures or recordings which contain libelous, slanderous, abusive or defamatory statements, or racist, pornographic, obscene, or offensive language;
  • you will not forward chain letters through the Service;
    d. you will not use the Service to infringe the privacy rights, property rights, or any other rights of any person;
  • you will not post messages, pictures or recordings or use the Service in any way which
So...we delete users who don't follow our very basic privacy policy. Does this make them unfit to date? Well, it makes them dumb and somewhat conniving -- two things I'm not personally looking to date -- but ineligable for dates of any kinds seems harsh -- and that's coming from a girl who views men who wear chain lacklaces as unfit to date.
Verdict: Plentyoffish -- not to be trusted.

But back to this issue of determining who's fit and unfit to date. This would be helpful -- very helpful. If I’d had previous knowledge of certain people’s lack of dating fitness I’d have avoided starting or perhaps stopped trying to date them. But – and this is very big of me to say – unfit to date me and unfit to date are potentially different things. Guys I’ve branded unfit have actually gone on to successfully date other girls…aanndd guys.

Is there a person out there who is guaranteed to screw you over? Probably. Some guys are players. Some girls are liars. And vice versa. But I tend to believe that’s all just circumstantial until the right person comes along.

To be completely unfit to date you’ve got to really have something going on. Recently divorced? Yeah, should probably take it easy for awhile, but what if it was a long time coming and he’s already moved on? Small time crook? I mean not the man for me, but what if some female small time crook is looking for a con man mate? Pathological liar? I’d agree that is a problem, but who’s going to admit that to some online info fields?

I'm not saying I don't have a dating dealbreaker for every letter of the alphabet (3 for "s"...), but could I deal with S, Short if I came across a more important deal enhancer like M, Musically inclined? and H, Handy? I'll get back to you on that. You get back to me with what circumstances you think make someone undeniably unfit to date, anyone (
In the meantime -- feel free to vandalize that PlentyofFish crap whenever you see it.

Monday, May 11, 2009

Experimentation, Foundation, and Legacy.

*Dani, this one's for you and the girls.

I heard an accomplished media executive speak about her personal life journey last week. She was, at 25, almost exactly where I am now -- a single, apartment- dwelling media agency person with a dozen side projects and a 24-hour-style life.

The focus of her talk was on the tent poles that defined her journey – those cross-roads or decision moments where her perspective changed – by her choice or not – and everything from then on shifted.

At 45 you can scan back and evaluate all the parts that have lead to your whole. You can say – “there, right there was when I really knew I want to be a ______________.” Or, “now that I’m through it I can say that _______________ gave me strength to know I had to _____________.” And, “If I’d ______________ before I _______________ I never would have _______________.”

At 25 there are less than a handful of things I can turn back and say something like that about. I have learned lessons. I have overcome obstacles. But the biggest decisions I’ve made so far have been what to study in college and where to move once I graduated. I’ve since stuck with my chosen industry...and my chosen apartment.

But according to the speaker I heard last week – that’s all about to change.

I am (we are?), she explained, lingering in phase one of the three phases of adulthood. From about 18 ‘til now we’ve been in what’s termed the “experimentation” phase. Life is, for the most part, one big test lab. Yes we’ve put some stakes in the ground – gotten expensive degrees, invested time in a given career, experienced serious relationships – but it’s all still open to negotiation. We are only responsible for ourselves. If an opportunity abroad came knocking, we’d say, “what have I got to lose?” If we were miserable in our jobs we’d say, “I have no reason to stay in this field.” If things got rocky we’d break up and our Mom’s would say, “thank god they didn’t get engaged.” We are transient. And when you’re transient you do things like buy four new pair of shoes in a week because looking great at several upcoming cocktail parties actually seems a smarter investment than an extra 200 bucks in your Roth IRA.

Pretty soon though, the speaker warned, it will be time for phase 2 – foundation.
Foundation is where you start to freak out about the fact that 50% of your friends are married and or own property. You have likely surpassed the age you were when your parents had you (aanndd your first sibling…) and yet you still can’t fit your summer and winter clothes inside your apartment at the same time. And so you start looking at that maaaaan in the mirror and asking him to chaaaaange his waaaaays.

Those changes of ways tend to come in the form of saving money, making strong advances in your career, and locking it down relationship wise. It’s not that you don’t want to keep experimenting or that you’ve tested all you’ve wanted to – it’s just that the group veers left towards dinner parties and away from vomiting at 2pm during a work day because you have to do those things if you want the rewards of a healthy, stable future. You grow up. Not because you have to, but because you want to. This, we will learn, is a good things because it gets us to phase 3.

Somewhere in those foundational years among all the saving for retirement and buying of matching china your gaze shifts toward the "what it's all really about" – legacy.
It’s tends to start with having kids and end with heading up charity organizations, but suddenly who you are to the world you’re leaving behind becomes more important than who you are to that existential self – that 25-year-old self who just wanted to be happy and motivated and fulfilled by personal successes. The legacy portion is where we calm the fuck down and realize no one will remember how late we stayed out from '07-'09 or how many cool restaurants we had on our "been there" list.

I was starting to feel like a real asshole – albeit in adorable new yellow canvas wedges -- as the speaker finished up explaining the legacy portion of her lifeline talk. Seems it’s only a matter of time before the ghost of experimentation’s past is going to arrive in the night to burn my new set of summer scarves and show me what happens to girls who don’t save 10% of their pay?

Apparently, the timeline wasn’t the point.

We do it in steps – experimentation, foundation, legacy – because we can’t generally see the forest through the martinis. We’re here and now people. Followers of jumpers off bridges. It's just easier to have one motivation at a time -- especially when right now it's about experimenting...

But the point of the three phases is that you're supposed to do them together. You’re supposed to keep experimenting while building a foundation with an eye toward our legacy. Yes it gets harder and harder to overhaul your career the older you get. Of course people come into our lives to make it less “all about us.” But this attitude of “I have to pack it all in now before it’s all over” is dangerous. It makes us do things that weaken our foundation and tarnish our legacy – two phases we can’t stop from arriving no matter how hard we experiment.

No – the talk didn’t change my life overnight. There was this straw hat I totally couldn’t resist at Urban Outfitters that I absolutely do not need. But now I have one of those wise-sounding phrases to add to the talk I’ll give someday.

“I remember hearing this speaker talk about the three major life phases when I was around 25,” I’ll say, “and I knew then that I had to change the way I think about where I am today and where I want to be someday.”

Friday, May 8, 2009

Would You Rather: divorced or with child?

Let's take this week's theme one awkward step forward.

Would you rather date someone who's divorced
or someone who has an illegitimate child?

To be clear.

The someone who's divorced was married but is no longer. Doesn't matter how long they were married or why they got divorced. They have an ex person (wife or husband) who is somewhat in their life.

The someone who has an illegitimate child was never married to the child's other parent. Maybe they dated for awhile. Maybe they never dated. What's important here is that this child is in this person's life -- visitation rights, child support, birthday presents.

Apologies up front for positioning both of these issues as a problem, but I think we can all acknowledge they're not ideal and as such debatable.

So -- things to consider:

The divorced person got all the way married. Dated someone for a presumably long time. Proposed to said person or accepted a proposal. Endured months of wedding planning and then walked down or stood at the end of an aisle and said "I do." I realize these things can carry you away. I also realize that things happen that are beyond your control (cheating primary among them) that make divorce a smart option.

Did the now divorced person "make a mistake?" Not necessarily. They may have fully believed this person was the right person and been proven wrong by unknown circumstances. But maybe they did make a mistake. Married for the wrong reasons? Married too young? Who knows.

Now the illegit parent is a totally different situation. This person had sex that resulted in a child. Was the sex with someone they loved but decided they don't want to marry? Maybe. Was the sex with someone they barely knew? Could have been.

People get pregnant, have children, and never even notify the other parent. In this circumstance, no matter what the relation of the two people before baby was born, this parent was notified and is now responsible. As such they are involved. They have a child. They always will.

What's interesting about this is that it's actually easier to find yourself with an illegit child than it is to find yourself married. That's a -- technically speaking -- easier mistake to make. And yet it results in someone far more difficult and lasting. An ex wife or husband is awkward and complicated and sometimes expensive, but you don't have to deal with them in the same way you do a kid.

And then you have to layer in the fact that there are value systems involved here. If someone has a kid out of wedlock that means they chose not to abort the pregnancy. Whether the person is a woman and personally made that choice or the person is a man and supported that choice -- it was made. On the divorced side -- the person decided to get divorced. Maybe there was absolutely no saving the marriage. Maybe there was a failed attempt. Maybe there was no effort involved. Either way -- there was a choice, in both circumstances.

Loaded questions for a loaded issue -- one (or both...) of which was maybe the fault of really loaded people.

Which would you choose?

Wednesday, May 6, 2009

Would you rather: hear "no, not interested" or walk away without knowing?

My friend and I were catching up about the verdict on a guy who’d been giving mixed messages for the few weeks they dated.

He’d return calls and texts (eventually) but not really initiate. He’d agree to dates and plans but never take it beyond a good night kiss. He seemed interested but after several weeks of no real moves it was pretty unclear.

I’d given my friend the advice I usually give in circumstances like these. 

Walk away. Send a final – "hey, seems like you’re busy lately so let me know if you’re up for hanging out again" message (text, phone, email) and then let the other person decide. Drop the ball off in his court. As (extensively) discussed – if someone likes you it should feel like they like you and want to make that clear. It shouldn’t feel like you’re confused every day if they ever remember they’re seeing you.

But my friend is a more committed person than I. He liked this guy. And more importantly – if the answer was “no, not interested” he wanted to hear that before he gave up. “I’m very stubborn,” he’d told me the last time we were chatting about it. “I’m not going to give up on this so easily.”

Would you rather walk away and assume the answer is “no thanks” 
or would you rather keep going until you know “no” for sure?

With the former you’re protected – as in, you never have to hear “I’d really prefer we just be friends” but you have to deal with the gnawing question of, “did I just give up too easily? Did he/she think it was me who wasn’t interested?” should I have said, “hey, I’m really interested here, where do you stand?”

I want to stand firm on my “if you have to ask then the anwer is no” policy. And “you won’t know if someone is really interested until you leave the ball sitting in their court.” But people from the other camp – my friend included – ask why I don’t just want some piece of mind. You’re way too quick to give up, they say. If you really, really liked a guy why wouldn’t you keep going until you were sure there’s no hope?

Honest answer – because that set-up holds the potential to make me feel like shit and I make it a point to mitigate all potential feel-like-shit opportunities.  If on Monday I text you, "hey let me know if you're up for doing something this week" and the following Monday you text back, "hey, sorry, was swamped last week" I'm not concerned about how you feel about me.  At that point I don't like you.  

This - I realize - makes me cynical and quick to judge.  In my friend's scenario he gets a full guarantee that it's not going to work out.  He gets to say -- "I wanted something so I went for it and now I'm certain it's not going to work out, but I gave it my all."  With mine it's, "I wanted something then it didn't seem to want me back so I ducked out and will now focus efforts on avoiding this person for life."

Am I smarter or safer?  If my friend more stubborn or just braver?  Has anyone's mind been changed and behavior improved by being flat-out asked, "are you in or are you out?"  

My friend's guy just wanted to be friends.  It was what I'd suspected, and what my friend had suspected, even when he asked him.  "I'm just glad I know though," he told me.  

He'd rather be disappointed than always wonder.  You've gotta respect that -- especially if, like me, you could never handle it yourself.

Monday, May 4, 2009

Would You Rather: date a non-dater or a serial-dater?

You know how sometimes this happens:

  • You: Yeah, so he seems really incredible – like a really great guy.
  • Your Mom: Hhmm, that’s great. Why doesn’t he have a girlfriend?
And then you count from 10 to 1 before you say “probably for the same reasons I don’t have a boyfriend, Mom.”

What you’re really thinking goes more like – I know!!! I don’t know, but I have a pretty thorough mental list going. Right now I’m leaning towards – "has been very focused on career" with the possibility of – "divorced parents instilled cautions about quickly slipping into relationship."  But what do youuuuu think?!?!?!

Or better yet this:
  • You: So yeah, we’ve been seeing each other for awhile – I think I really like this one.”
  • Your friend: That’s so great. So what’s his dating history like?
  • You: You know, he hasn’t really had a serious girlfriend beyond his high school girlfriend.
  • Your friend: Oh…wow…and he’s 28 you said? Wow. Does that concern you?
At which moment you take a deep breath and gchat back, “I think I’d prefer that over him having a laundry list of exes” full-well knowing you don’t know what the fuck scares you more and would actually prefer had just appeared Starman style (minus the stone-washed jeans and lack of English grammar skills).

Would you rather be with someone with a long history of much dating 
or someone with relatively no history at all? 

Gut instinct for me -- the latter. Clean slate just seems safer. Maybe he was a little nerdy in high school and a little focused in college but now he’s finally coming into his adult own? Maybe he comes from a family of sisters so was raised to be particularly picky about his women?  I'd rather deal with those intangible maybes than very tangible former girlfriends with names and faces and jeans sizes.

See it's that or the potential of ending up one more 6-month test-run in a serial dater’s storied past. ‘Cause what’s that guy/girl doing wrong every time? And how am I supposed to know that they’re not going to tire of me like they tired of them? Did he go in every time thinking she would be the one but somehow she disappointed or does he just have no idea what he wants so everyone disappoints?

I admit there's something a little hhmm about a guy or girl who hasn’t been in a committed relationship in their technically adult life? With a chronic dater at least you know they have it in them. They can handle the motions, make the decisions, deal with the issues. Impossible to know how many times it was real and how many times it was just a here-and-now deal, but practice makes perfect, no?

Is our call on this matter not – I wonder – all just a reflection of ourselves and our own dating history? So say I'm of the “not much history at all” set (which is what you would if you knew me). I haven’t, in what we can consider my adult life, been in a relationship that I took home for Thanksgiving. I have yet to “meet the parents.” In my mind my lack of practice doesn’t make me a liability – it makes me a picky person (who lives in Manhattan). But what does it make me to the male world? A girl who doesn’t know how to be a girlfriend? A girl who doesn’t make relationships a priority?

For as many times as I’ve gone, “yeah, he’s great – but he’s just always needs to have a girlfriend – any girlfriend.” Is someone going, “she’s fantastic, but for some reason never has a boyfriend – you’ve gotta wonder about that…”

So - do you’ve gotta to wonder? Is there any significant difference? And if so then shouldn't there be some concrete numbers around it? Like a person with x amount of relationship under their belt is y percent more likely to succeed in long-term relationships, typically but not always on the z'th relationship.

I'd like to see those numbers...unless they make my own numbers a little too hhhmm...