The other day I was telling a friend about my three favorite girls in Manhattan. The countdown is:

#3 A cute waitress at The Bowery Bar
#2 The bartender at The Village Pourhouse
#1 A friend who I only get to hang out with once in a while in group

Upon looking at that list, I noticed a few sad things:

  • I have never talked to two of those girls
  • I don't even know two of those girls' names
  • The one girl I do talk to, I get along with great—and she flirts with me—but she has a boyfriend

The net of this is that there is no hope to get even one date with any of these girls. Is it just a coincidence that my three favorite girls in Manhattan are all impossible to date at the moment, or am I purposely longing for unavailable girls?

There are some major problems in the way I react to situations when things come easily. Whenever I find out a girl is interested in me, it chips away at my interest. I'm happy to go on dates with girls who ask me out, but I'm just not accustomed to a drama-less, easy experience.

The other problem I have is that I lose interest when I hear things like

"I have the best girl for you and she is soooooo single!"

Being single should be a requirement for girls that I am interested in, but it's not.

Instead, I tend to go for girls with boyfriends, girls who live far away, girls who my friends don't think are a match for me (sometimes even I know this, but I keep trying for these girls).

Am I suffering from Romantic Comedy Syndrome? Romantic comedies have taught me that happiness in a relationship usually comes with some kind of suffering or adversity. Do I need to find someone in a coma, or get picked up by some rich dream girl who makes me over...after purchasing me for gigolo services? Sorry, I haven't watched any romantic comedies since the '90's. But you get my point.

This against-all-odds mentality is what I've been working with lately. If a girl is available and there are no extenuating circumstances then there is no drama and I usually don't pursue it. If the girl is unavailable: has a boyfriend, lives in another city, has no connection to me—usually I haven't even talked to these girls, I just know of them—then I am intrigued.

Lately, I've been a sounding board for girls who are disgruntled with their boyfriends. So, things tend to move toward romance as I listen to these girls talk about guys who have cheated on them or who are boring them. I know I should keep a certain distance while trying to help, but it gets really hard sometimes.

I am a hardened therapy veteran. I've been through it all. One of the theories posed by one of plethora of therapists is that I have a fear of success. This self-defeating behavior is crippling in so many ways: relationships, work, personal growth. It causes me to shy away from things that might work out because I feel that if I don't make an effort than I have a built in excuse for not succeeding. Most of the girls I take an interest in are full of built-in excuses that will prevent me from going out with them and also not hurt my pride: "hey she was unavailable anyway".

So why do you think I'm doing this? Do you think that I am just not ready to make a commitment, and not ready for a relationship so I satisfy my instinct to go for girls by treading water towards unavailable girls? Am I afraid of what might happen if something actually works out? Or do you think that I truly just want a major challenge before I start dating someone? Do any of you find yourselves only going for unavailable guys? Have you ever gotten close to a guy who has a girlfriend after starting out as their sounding board to vent about that girlfriend? How do you handle this situation when it happens?

What Do You Think?