I'm through dating jerks but nice guys bore me

I want respect. But where's the spark?

By Cary Tennis

Published August 5, 2011 12:20AM (EDT)

Dear Cary,

I'm writing from work so this might be quick and disjointed, but here's the deal. A couple of years ago, I had something like a midlife crisis (though I was technically too young for one). I went through a depression. I ditched a super-unhealthy (emotionally abusive, even, according to my therapist) female friendship with my "best friend," the mean girl from high school. I quit my job as an adjunct professor and sold out -- but in a good way. I now have a cushy job that pays me three times what I made before and offers benefits. I'm less poor and less stressed out (if sometimes a little bored). I also went on this big quest to date nicer people instead of ones who ignored me or dissed me or told me I could stay in their apartment while they went on vacation and then didn't give me the key.

Therapy was a big deal for me -- I was depressed but also had a self-esteem thing that needed to be dealt with. Short story: My father is somewhat nuts, my mother is overly critical. I learned to be complacent and never say a word about my needs in order to keep the peace. I wasn't even completely aware I had needs. OK, fine. I took therapy super seriously and eventually, the depression got a lot better. I got back in touch with my instincts. I learned to be more assertive, I stopped taking quite so much shit and decided I wasn't an idiot in need of abundant help in the world. "Recovering doormat" is one way to put it. All of this is good.

I'm still having trouble dating, though. I worry that I just don't like these nice guys and I know that's f-ed up, but this is what's going on. Right now, I am dating an extremely nice man. We had a really, really fun first few dates. He's extremely good to me, if a little cheesy/overzealous. He's a self-professed dork and sometimes his insecurity (ironic, huh?) gets in the way of our actually connecting, in my opinion. I feel like there's a lot of depth and feeling and interesting stuff to him, but that's not what he puts front and center. I feel like I can see his lack of faith in himself, because I'm so familiar with that feeling. He goes on these tangents where I think he's trying to connect (long monologues about his life and past) but then he doesn't ask a ton of questions to me in return. It doesn't feel like a give-and-take, getting-to-know-you session but like he's trying to pass a test and somehow I'm the grader. This isn't what I want.

But I was willing to work with it -- I know we all have issues. He is a nice man and I'm trying to date nice men. And really I think he's cute and smart and funny. I know that I was raised in a critical home and can be critical of others and I really, really don't want that, so I don't want to be overly critical of him.

Anyway -- we've been dating for a little while now and at first, were just doing some light fooling around and the chemistry was great. I couldn't wait to have sex with him. And then we did. And it was really, really bad. I know that first times are often weird. I know that things get better, you get in sync, etc., etc. But the next day I found myself thinking, "Man, if that was all there was to sex, I can see myself never, ever having sex again." He just sent me a sweet email saying one of the sweet overzealous things he says, and whereas before I thought it was kind of goofy but nice, now I'm not feeling much. And I'm worried that all of this says something about my totally irredeemable dating habits and/or inherent inability to love and be loved. Yadda yadda.

Having been around a lot of assholes in my life and knowing how much it hurts to interact with them, I have a huge fear of being an asshole myself (still) and so I'm struggling here. I know the thing to do is to somehow say "Hey, Nice Man. I'd like it if we could communicate better ..." or something like that, and then "Hey, Nice Man, here's what works for me in bed ..." and to speak up about what I want and don't want -- but there's also a big part of me that kind of wants to go, Oh. No. Never mind. I'm struggling with the line between being open-minded and giving different people a chance, and paying attention to my instincts, and whether or not my instincts just aren't into it. Also, I run from so much of this dating stuff and I feel like that can't be helping me.

How do I fix this? I'm not even sure if I just made sense.


Dear Trying,

If I were you I'd want to find out what he is really feeling in the moment. Seriously: I would be curious. What is going on? Maybe he won't tell you. Maybe he's trying hard to make this work, so he wants to look good. But the act is falling flat.

So tell him it's not working. Tell him you know there's some other man inside there that's not coming out. Issue an invitation. Invite this other man to come out. Ask him to please, please, please just talk to you like a friend, like somebody who's on his side, who's interested in what he has to say. Let him know he's got nothing to lose.There may be things about you that he doesn't like but he's afraid to say it. There may be fears. I mean, there are always fears, right? There may be some hideous family history. So get everything on the table. Clear the air.

Don't expect magic. He may not open up right away. So keep at it. Tell him your history. Tell him how you've been attracted to abusive people, and how you like him because he seems kind, but you also want to tear into his guts and find out what he's made of. You know what I'm talking about, right? You know what it's like when someone is in turmoil and you're wondering what they really want to say. So that's my suggestion: deepen the relationship by pressing him to be honest.

My guess is that each of you is at a turning point. At a certain stage in life we're trying to nail things down. We want to meet the right person, have the right sex, get squared away. So we tend to see each person as a potential lifetime mate and that's that. But if you look back over your life, you see that many people in what you might call "failed relationships" actually taught you something. This mean friend you had. Your critical mother. Your dad. Your therapist. You were learning in all those situations and you're learning now. So use this opportunity to learn.

He may not be the one who becomes your lover and satisfies you sexually and sticks with you. He may not become your husband or long-term mate. But you are trying to do life in a new way and he's your first attempt. You're trying to live not as a doormat, not as a sidekick but as your own evolving person, full of self-respect and dignity. So give it a try.

Here's another thing: Do you have to be monogamous? Do you have to restrict yourself to having sex just with this one man you're currently dating? Maybe your relationship with this man is not about the sex. That doesn't mean it's a failure.

This may be a great time to make another appointment with that therapist who helped you get over your depression, and work to map out how this new relationship is triggering some of your old problems.

Maybe you won't fix the sex. But you can learn how to be completely honest with another person and manage the relationship so it feels like a good, straightforward experience: something that happened on your journey. Something you went through with dignity and kindness and strength. Something you can look back on with fondness and pride.

Citizens of the Dream

What? You want more advice?


Cary Tennis

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