Q: Dear Meredith,
I am currently single and have been for about three years now. I am 28 years old. I dated and lived with a great girl previously for about a year, but it didn't work out.
Back to why I am writing you. I am totally lost and hopeless in the dating arena. I have so many issues. I think I am attractive, in good shape, have a good job, and am very honest. But sometimes I think maybe I am trying to go out with girls who are too "attractive," at least based on my definition (not everyone agrees). When I say, OK, let me try someone who maybe I am not attracted to but could be good for me, I am totally not into it and end up feeling I wasted my time and hers. So that's one issue. Am I attracted to girls who are out of my league?
The more important issue is that while I actually do pretty well with getting dates and meeting women, I drive myself absolutely CRAZY with (1) when to call, (2) when to text, (3) when to meet, and (4) freaking out that maybe she doesn't like me and on and on and on. I self-destruct. I could go on an awesome first date but then smother the girl, texting the next day what a great time I had, asking her to go out again right after, and trying to contact her too much. One girl said that she got a sense of paranoia from me and that I could be insecure. Others say that I am too forward sometimes. I am just trying to be honest when they ask personal questions. I feel like it is more anxiety than anything! Friends always tell me to play it cool, but I totally can't. I already met a cute girl and asked for her number, but I am afraid I will screw it up again. I know others have much bigger problems, but I feel like a lot of my issues are what single guys and girls are often feeling -- when to call, what to do, etc. It feels like everything is magnified at the beginning so when being too careful, I actually mess it up. I probably sound desperate!
Please help ... I just want to meet someone and settle down. I am 28 and not getting younger!
– Totally Lost in NYC
A: Your first problem doesn't bother me, TLINYC. You should be attracted to the people you date. And you seem to be finding plenty of women to pursue, which means that you're not being too exclusive.
As for your second problem, it's true, you do sound a bit anxious and intense. You want to go from 0 to 100 with women after one date. That's not good for anybody. You can certainly call or send a text to thank someone for a nice night out, and you're allowed to be nervous when you hit the send button on your phone, but not every date is going to turn into a relationship. And if you don't see a woman right after a first date, it doesn't mean that she's going to disappear.
You mentioned that you come off as too "honest" on dates. I have to wonder whether that really means "self-absorbed." Yes, these women are asking personal questions, but there's no need for ridiculously long answers on a first date. And I would hope that you're asking these women just as many questions about themselves.
You seem like you might be obsessed with your own needs. What about theirs? Are you listening?
It's also important that you surround yourself with single friends. Couples are fine too, but this whole "I'm already 28!" thing means that you've lost perspective of what it means to be your age. Hanging out with peers will remind you that there's no need to rush any of this.
I want you to be so busy with friends that you only have one or two nights a week to date. Plans with friends will stop you from trying to see a woman 14 times in a row. They'll also keep you from feeling lost. That's important, especially in New York City.
Readers? How can he deal with dating anxiety? Am I right about the self-absorbed thing? How do you get out of a three-year lull? Discuss.
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Meredith Goldstein is a Boston Globe columnist who follows relationship trends and entertainment. She offers daily advice on Love Letters — and welcomes your comments. Meredith is also the author of "The Singles," a new novel about complicated relationships. Follow Meredith here and on Twitter. Love Letters can be found in the print edition of The Boston Globe every Saturday in the G section.