I Haven't Dated Since High School

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QDear Law Firm 10:
I’m a lawyer who dated the same woman since high school, but—long story short—we are no longer a couple, and I’ve recently been thrown out into the dating world without any experience. I really do mean without any dating experience whatsoever, except whatever you call dating as a high school sophomore.

I’m now 28. Since breaking up with my girlfriend nearly a year ago, I’ve been on a few dates, but whatever I do, I cannot seem to get past the initial date (maybe three dates at most). From what I can tell, it’s because I’m too slow. Maybe shy, maybe I’m out of my league, but it really comes down to not knowing what to do. Which is my question: do I take it slow? In other words, do the whole high school thing of holding hands first, then kissing, then moving on—the whole first base, second base thing, kind of like a progressive dinner?

Honestly, it really doesn’t seem to have changed much since high school, which is kind of funny. Or has it?

AHere’s the problem. It’s one thing to have only dated one person from the onset of puberty until you’re on the brink of 30, such that you’re a little jittery and rough around the edges when it comes to dating. That’s completely understandable, and I can drum up an appropriately human amount of sympathy for that sort of predicament. But it’s another thing altogether to remain functionally frozen in time during a 12 year relationship, and that seems to be the root of your problem. I mean, for the love of god, man—you referred to first and second base and holding hands in your question. Clearly you need to do a decade’s worth of evolving before I could be of any real assistance to you.

But I will try nonetheless. First things first: things have changed a lot since you were in high school. For starters, the odds are extremely high that any girl you go on a date with has had sex many, many times. So if you try to hold hands with her, or—worse yet—if you start hooking up with her and going up her shirt is your climactic move, she is going to be very turned off (and perhaps even a little bit freaked out), and she will then proceed to completely forget about you in less than six hours. (Unless of course she is extremely unattractive, in which case she will convince herself that you’re sweet and shy and worth sticking around for, since—let’s face it—it’s not like she has any other suitors lined up.)

The most important thing for you to keep in mind, though, is that you’re getting close to 30. Which means that the girls you are going on dates with are also probably getting close to 30. And women on the brink of 30 are inching pretty damn close to being squarely behind the eight ball in the dating realm, which leaves a 28 year-old man like yourself in a fairly comfortable driver’s seat, so to speak. So sack up and remind yourself that they need you more than you need them before you show up for a date. And don’t psych yourself out when it comes to getting physical. Take the lead and enjoy yourself. Chances are, she is more worried about whether you’re having a good time than she is about herself (at least during the initial hook up sessions). Check back in with me if you make it past 10 dates and we’ll work on the advanced stuff.

Have a dating or relationship question for Law Firm 10? Send it to editor@bitterlawyer.com and put “Question for LF10” in the subject line.

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