It always leads to sex

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I'm 35 and have two teenage kids and am divorced. I've been single for 10 years – sort of. I've dated on and off over these last 10 years, but no serious relationships. I'm pretty sure the problem is me. I notice that I self-sabotage. There's one red flag and I shut it down, or I sleep with them on the first date and then feel ashamed, or disrespected, or like I disrespected them, or ... whatever. Some of these guys have been really nice guys, but I always feel really pressured right away.

I know that I'm grown and have the capability of saying no, but it's easier to give in and then ditch them. I really dislike online dating but I do understand it's the most common way to meet someone. I find it overwhelming. I find that I want to give everyone a chance but the conversation are either sexually charged, or just really insipid. I want something real, something long lasting but how do I get past myself?

– Sabotage


First, therapy. If you can talk about shame and self-sabotage with a professional, you might gain some tools for connecting with other people in a way that makes you comfortable. This pressure isn't good for you.

Second, maybe apps aren't for you. Really. Yes, they make it easier to meet a lot of people at once, but the back-and-forth happens quickly. Sometimes there's this need to figure stuff out in one night so everyone can move on to the next swipe. You're having trouble making significant connections, so you might need to find a method of meeting people that allows for a better pace. In a more open world, there are clubs, activities ... more ways to engage. Start by signing up for a few groups (in person or virtual) that allow you to actually talk to other people, even if they're not single. It’s all about expanding your network. If you like a sport, books, movies, etc., find likeminded people.

Third, dates can happen at lunchtime. They can be walks. Haven't we learned that during the pandemic? If you really want to talk, without the talk being about what might happen after dinner, get outside and do an activity with someone. Find a new way to bond. One idea (if you're in or around Boston): the deCordova Sculpture Park. You can chat about the weird looking stuff on the lawn.

Please keep us posted – and good luck.

– Meredith

Readers? Thoughts on how to date without this pattern continuing?