I Didn’t Date For Years

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Hi Meredith,

I’m a man who recently got back into dating in my mid-30s – after not doing much of it since high school. Lack of confidence plus a lot of moving around the country in my 20s caused me to avoid it altogether. How can someone like myself bridge the gap, now that I’m going out with women who have been actively dating for 10 years? I feel infantile in my approach and too shy to make physical contact, and the whole process has been intimidating.

I met a really nice woman recently, and I’m feeling clueless about how to communicate, read signals, or guess where we stand after going on three dates in five weeks. I feel like things should be progressing quicker, and she’s not open with me about her personal life, whereas I have been about mine.

I think part of my issue is that it’s hard for me to attempt to get physically intimate if I don’t feel a connection. My circle of guy friends would laugh at me for saying that, but it’s true. My gut tells me this woman probably isn’t compatible with me if she doesn’t value honesty and seeing each other more often, but I also feel like this is one of my few chances to meet someone and should roll with it. Is this all in my head? Does the fact that I haven’t dated in so long (or really at all as an adult) make me a less desirable companion to all those that have?

– Rolling With It


Many people in their 30s have spent the last 10 years swiping on apps, having first dates, getting ghosted, hitting a wall, and feeling like they’ll never find someone who’s ready to listen and connect. They have dating fatigue, a thing we talk about a lot here.

You don’t have that. That makes you … refreshing? You’re not playing by any weird rules. You’re not desensitized to good company. If you’re clear about what you want and what you’re wondering (questions are good), you should impress a lot of people.

If you’re nervous, say so. If you’re wondering about a kiss, ask. Bold honesty can make a date night go very well.

This particular woman doesn’t sound like a good match for you, so move on – before you work too hard to make it something it isn’t. That kind of effort can give you dating fatigue. Tell her you get the sense she has a lot going on, and that you haven’t felt like it’s made sense to take it to the next step. Wish her well and be nice.

Start having dates – app first dates, setups, etc. – just to have them. Remember that people coming out of long relationships might feel just as inexperienced. They’re also figuring out how to be on their own – something that comes easily to you.

Don’t feel bad about needing some emotional intimacy before the physical stuff feels right. I bet some of your friends feel the same way. You’re not waiting to kiss someone until you feel a deep bond that takes years to build; you just want connection – something to suggest you’re sharing an experience. That’s OK.

– Meredith

Readers? Pep talk for dating? Is it worth asking this woman what’s happening?

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