Week 3: Knowing What You Want vs. Being Picky

My cousin Emily was the Matchmaker for Week 3, and when we were wrapping up her Matchmaker week I asked her if she has any dating advice for me.  She said a phrase that I've often heard, which most single people dread:

"You need to figure out what you want."  

I like to think I know what I want, I could write a page or two of qualities that I'm looking for in a guy.  But then I feel like people would tell me I'm "too picky."

Is that the fate of the single person, you "need to figure out what you want" but if you know what you want you're "too picky"?

I know some people get too focused on specific (often superficial) details.  If I'll only date brunette millionaire Harvard grads who are 6ft or taller, I'm significantly reducing the number of guys I can date (especially since I'm not in millionaire and/or Harvard social circles).  But if I want to date an emotionally mature, financially stable, kind, down-to-earth guy with a good sense of humor, am I being "picky"?  Where's the line between having standards and having a laundry list?

Emily said that she had been too picky, so a few years ago she decided to give everybody a chance and it helped her figure out what she really wanted.  She and her boyfriend had known each other for several years through friends and they initially didn't get along very well.  As they spent more time together she realized that she liked how she felt around him.  And he fit other criteria she had: physically active, independent, doesn't play games, and she didn't have to give up her high heels.

One goal of this experiment is to give guys a chance that I normally wouldn't.  But my dating history suggests that I could be a bit more discerning.  In the past 6 years of being "single" I've dated/been involved with a wide range of guys: hippies who lived in buses, anarchists, a writer/director, an accountant, a bartender, and a compulsive liar.  I was trying to be open to anything and along the way some standards developed: I will only date guys who live in a permanent structure (house, apartment, etc), no long-distance, must have compatible senses of humor, not bats#%t crazy.

I prefer to date guys that are taller than me, and some people seem to consider that "picky."  Is being "picky" about physical/superficial things?  But attraction is at least somewhat physical/superficial, and how much can we change what we're attracted to?  No one will match every quality you're looking for, but where is the line between compromise and settling?  How about the differences between the type of guys I say I want to date and the guys I actually get involved with?  Lots of questions to ponder...


At the end of her Matchmaker week, Emily picked two guys:

Bachelor #6 is a church-going music teacher who says he's a good listener (interestingly, he is from Georgia, where Emily currently lives).

Bachelor #7: Emily described him as a male version of me, in his profile he says he's "A witty, goofy, introspective, serious spaz."  Differences between us: he's 39 years old, one inch taller than me, and has a red "Jew-fro."

She said they both "seemed intriguing and not your normal choices, but not going to piss you off either."  I contacted both bachelors, and Bachelors #6 and I are working on scheduling a date.  Bachelor #7 has not responded, so the trend of one bachelor per week being a flake continues.  It is odd to me that it's such a high flake rate, but thankfully I just see it as a statistic of the experiment and I don't take it personally!

We also started a new Matchmaker Week!  The Matchmaker for Week #4 is my friend Michael.  He and I went to high school and part of college together, and traveled in Europe together during college.  He's the first male Matchmaker of the experiment, so we'll see how his perspective is different!