I’ve realized this of late.  It’s expensive, it’s exhausting and oftentimes, it’s fruitless.  I suppose I’ve been more avid about dating lately because it dawned on me that I haven’t been in a relationship for well over 5 years and being in a relationship is a rewarding and lovely thing and frankly, I’m far too awesome to not have an awesome girlfriend.  This isn’t to say that I’m approaching women in bars with a look of despair in my eyes and begging them to see how great of a person I truly am…I save that approach for my online dating…(mostly) kidding.  It’s just that I’m open to the idea of a relationship where I haven’t been in the past and I’m giving myself more opportunities to be presented with that option.  However, there are a couple problems with my approach to dating:

1. I’m very picky.  I expect a LOT out of someone in a close relationship with me, be they friend or girlfriend.  This is the reason I’ve had the same close circle of friends for damn near a decade now – they are amazing, unique, intelligent individuals who all add value to my life and know and care for me and have my best interest in mind.  I have to truly respect you to let you into my inner circle.  That respect is borne out of combination of things, but briefly, you need to be funny, intelligent, caring (on a macro and micro level), and very importantly, I need to be very attracted to you.  I don’t mean you need to be objectively a perfect 10, I’m nowhere close (unless a 9 is close, then yes, I am close) but I need you to be beautiful to me.  And that can come in maaaaany different packages as I’ve dated a variety of ages, races, heights, etc.  I guess this boils down to three main things: be physically attractive, be funny and be smart.  Sounds simple doesn’t it?  Apparently not.

I feel like I’ve found so many women in LA that are extremes of certain characteristics that I look for in a woman, but rarely is there a balance.  For example, if a woman is intelligent, we spend the entire time talking about politics and civil rights and who’s gonna be the first to start the revolution and I’m left sitting there pondering the comedic genius that is potty humor (seriously, the word poo in and of itself is hilarious….replace shit, poop, dump or your favorite defacatory descriptor with poo…hours of laughs).  OR…if she’s sarcastic, which I often get confused for being, we spend the entire night trying to one-up each other, a competition she is bound to lose and find me more attractive in the process, and I’m left feeling as if I just went through 4 rounds of tryouts for an improv comedy team, it’s exhausting being this funny.  But I don’t necessarily feel that #1 is the problem for me, everyone should be picky about who they choose to be with so they can give their whole self to them, it’s that it’s coupled with #’s 2 and 3 that make it an issue.

2. I’m shy.  Those that know me well would completely disagree as I’m typically very outgoing, personable and likeable; but those that know me best know this to be true, I am a shy kid at heart, emphasis on heart.  I have no problem asserting myself in a family, friendship, acquaintance or even professional setting – I mean Sweet and Sour Jesus my job is to call strangers all day and try to convince them to trust me to get them a better job, you can’t be shy and be good at this, and I am good at my job.  However, I think I tend to compartmentalize those things a bit differently, even if it doesn’t make sense to do so.  If I upset my family or friends for something I do or say, I know they love me and we’ll get past it and I’m not shy about voicing my feelings or even admitting I’m wrong (I’m ready and prepared if and when this moment happens).  If I say or do something that causes an acquaintance or a friend of a friend to dislike me, my response is often either a). they don’t know me, I don’t take it personally or b). that was hilarious, fuck ‘em if they can’t take a joke.  At work if I get hung up on, or someone tells me they don’t want to work with me that’s fine, they have their professional interests at stake and I respect their decision to stay put or work with another recruiter, I don’t really take it all that personally (unless I’ve put a lot of time and effort into working with them and they screw me, in which case they are heartless douchebags and I hate them and all their friends).

But like I said, it’s different for me when it comes to approaching women and it always has been.  I take it personally if a girl doesn’t like me, even if she doesn’t know me.  If I find a girl attractive and I talk to her, I’m very likely much more reserved than I typically am because I want her to like me and I’m so invested in her judgment of me that I pull back and put on the doormat nice guy act so there is less to judge.  Without sarcasm there is less negativity, less of a chance something can be taken the wrong way, less of a chance something can go wrong.  It also seriously hinders the prospects of something going right.  Cognitively I know this, but I want this girl to like me, so I act more shy (read: boring) and consequently get passed over as a serious option.  However, a lot of this shyness is in the initial phase, the introduction or the getting to know you phase.  This leads to my last, and possibly most problematic flaw in my approach to women.

3. I don’t go after what I want.  If I get introduced to a girl or meet them in a social setting where most people know each other (so no, not Cheers, as I do not know her name) and there is no obvious agenda to my approaching her, then I’m fine.  We can talk to each other in a friendly manner with no necessary intent of needing her to decide quickly if she’s interested in continuing to talk to me or not; we’re just hanging out.  Alternatively, if I am in a bar/club and I see a woman and notice that – a). damn, she’s fine; b). she’s got a warmth about her, good energy, seems nice and cool (yes, I realize I just described a dream girl as both warm and cool…told you I was picky); and c). GOTdamn she’s fine – then I freeze.  Why?  Great question.  She clearly meets the preliminary criteria of what I want, so why don’t I go after it?  It’s a combination of things.  Part of it is ego and shyness – namely I think I’m pretty awesome and if she doesn’t agree then I take it personally and that sucks so why put myself in a position to be rejected.  But part of it is not wanting to come off as so blatantly transparent.  I consider myself to bring a lot to the table in all my relationships (friend, girl or otherwise) and I hate to simplify my interest and what I am to such a primitive emotion, especially since I know NOTHING about her other than how she looks from across the room.  In my head it always plays out as:

Me: “Hey, so I thought you were hot from over there….so I’m over here now.”

Her: “Oh….hi.”

Me: “Hi!….guess I shoulda thought through the rest of what I was gonna say.”

Her: “Probably woulda been a good move.”

Me: “Well then…um…you having fun tonight?”

Her: “Yeah….why don’t you go back over there and give this another shot-”

Me: “Oh, haha, ok like a do-over, cute.”

Her: “-with someone that’s not….me.”

Me: “Less cute.”

I’ve shared this bizarre, made-up scenario with several women I know and most of them say something to the effect of “that is sooo adorable, you should totally do that, if she’s cool she’ll appreciate your honesty”.  I have yet to try it.  More than anything I need to take the thinking out of it.  It really is analysis paralysis – or as the intro to Gin And Juice from Snoop’s Doggystyle reminds us “study long, study wrong”.  I’m too invested in the outcome at this point that I genuinely have to not care what happens in order to just be myself.  As a result, I have no problem charming the poo (funny? yes indeed) out of women I’m not interested in but those I do want I don’t go after for the most part.  The few exceptions are the instances described at the start of #3 where there is no pressure to do or say or act like anything and those are few and far between mostly because I’ve had the same damn circle of friends for almost a decade and we pretty much know everyone the rest of us know.

The one area where I’ve been completely comfortable approaching women without knowing them at all is via online dating (whatever, most of you have done it…and to those of you that haven’t you’ve all been on a date and you’re online right now, I just took it one step further).  The reason this is “safer” in a way is a). it’s not face to face and it’s not as soul crushing when you get a no and b). you can see so much about them (and vice versa) and display your true personality in your first interaction with them, which happens to be my strongest attribute.  The results are sometimes less than desirable but they do make for funny stories.

I think the problem inherent in my dating strategy is that because of the fact that I’m shy and I don’t go after what I want, I make concessions in my picky nature in order to date (as dating can be fun and the potential for a relationship is always exciting) and this ends up biting me in the ass in the longrun because ultimately they are not what I wanted in the first place.  This brings me back to my original point.  I tend to date way too much because I oftentimes go out with women who may not be exactly what I’m looking for.  This leads to more first dates and second dates but far fewer third dates.  ”Well,” you say, “clearly you’ve at least partially removed your head from your ass in this little diatribe, now you know what you need to do, so go do it.”  Yes and no.  Conceptually I know I need to be more assertive with who I go after, or at least be aware of what certain situations are and will be, the application is a bit tougher but well worth it.

For example, I recently went out with a woman 10+ years my senior who I’ve known for quite some time.  We both know we are at totally different places in our lives and know that any kind of relationship is out of the question.  But we’re attracted to each other and we enjoy each other’s company and you know what?  We had a blast – this is precisely what I’m talking about when I mentioned the importance of being aware of what certain situations are and will be.  Compare this with another date I recently went on with a girl who was very attractive and nice enough but I could tell had very different values than I did (namely, I valued intelligence and she did not).  We went out a couple times, I had some doubts and like I tend to do when confronted with an attractive woman who I’m not totally enamored with, I went out with her again.  It was in the middle of this date that my hunch was indeed confirmed based on a conversation we had.  We were talking about our families and the topic of being a big brother to my two younger sisters came up:

Me: “Well I’ve never really had to be all that protective of them since neither one has, to my knowledge, had a serious boyfriend.”

Her: “Really?  How old are they?”

Me: “22 and 24″

Her: “Wow…well what if they are lesbians?  Like, what would you do if they came to you and told you they were a lesbian?”

Me: “Um, love and support them.  I might be a little shocked initially but they are my sisters I love them no matter what.  You say that as if there’s something wrong with being a lesbian….what if your brother came to you and told you he was gay?”

Her: “No.”

Me: “What?”

Her: “Nope”

Me: “What do you mean no?  What if he came to you and told you he was gay?  What would you do?”

Her: “I would take him out and get him some pussy.”

Me: “And what if he said ‘No thanks, I don’t want pussy, I prefer dick’?”

Her: “Wouldn’t work, unacceptable.”

Me: “What the hell do you mean?”

Her: “Look, I’m not homophobic, I just don’t believe in homosexuality.”

Yes kids, for those of you scoring at home, my date did indeed say, “I’m not homophobic, I just don’t believe in homosexuality.”  Wow….just….wow.  Ignorance beyond ignorance.  At this point the civil rights lawyer within me started doing pushups and shadowboxing in preparation for a fight but I calmly finished my drink and as we were both fairly tired, suggested we call it a night.  Just for kicks, let’s briefly explore the lunacy of that statement.  Mirriam-Webster defines homophobia as the “irrational fear of, aversion to, or discrimination against homosexuality or homosexuals.”  In her mind, she probably rationalizes it as “I’m not afraid of gay people, I just don’t believe they’re really gay cause it’s not natural and they must have made a choice.”  However, when you “don’t believe in homosexuality” you are completely discounting their way of life, which is certainly discriminatory and absolutely falls under the definition of homophobia.  Don’t the homosexual acts of the members of the anti-gay Christian right prove that one’s sexual orientation is not a choice?  (Bill Maher makes this point in his “Dickheads of the Year” article for Rolling Stone)

*Steps off soap box*

In any event, I suppose I’m saying all this as a means of challenging myself not to date for the sake of dating in hopes that the B candidate will somehow morph into an A+ with a trip to El Cholo and a couple margaritas.  I’m challenging myself to either really go after what I want and be truly excited about dates I go on, or cut that shit out and go out with people I know I’ll have fun with, even if there’s no potential for something serious.  Something I’m sure both my wallet and my ego will appreciate.