‘Dating In Boston Has Been Rough’

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I am a 29-year-old woman and have been single for many years. In my last relationship, I threw myself into his life and pushed aside things that were important to me. I didn’t see it then, but he didn’t prioritize me or my interests.

Now I am dating, but nothing has stuck, and I worry that I will continue to be single forever. Dating in Boston has been rough; most of my dates from the apps turn out to be duds or people who lied about details on their profiles. I have tried to be open-minded and swipe on people I wouldn’t have in the past, but it’s not making a difference. The other part of things is that I am a sexual person, but my oldest sister (37 and married) has told me before that I shouldn’t sleep with people early on in the dating process because “I will give them the wrong idea.” My gut tells me that the person I want to be with wouldn’t be swayed by this, and if they are, they aren’t the right person for me.

But as the number of men I have dated rises, I wonder if she is right. Almost all of my friends are married or engaged and it’s getting hard to be the 5th, 7th, or 9th wheel all the time. I talk to my therapist about this a lot, and I try not to focus on it so much, but I still have a nagging feeling in the back of my mind that there is something about me that is undatable, and I will be alone forever.

– Serially Single


There are many 29-year-old single people who are looking for partnership. A bunch of them feel like there’s no hope – until they meet the right person and something sticks. Nothing I read about this letter makes me think there’s an unusual problem here.

Please know that there are so many available people at 29 (in cities) that it can be difficult for them to stop and decide, “OK, let me give this one person a chance.”

Please accept that there will be ups, downs, moments of exhaustion, and nights when you feel great about going home alone. There’s a reason they make movies with main characters who are just like you. From the outside, it looks pretty exciting.

I wish I had more to say than that. It’s exhausting – hence the whole category in this column marked “dating fatigue” – but at least you know it’s normal.

I do not agree with your sister, by the way. The “idea” you’re giving these people is that you like sex, and you do. I get no sense you’re confused about what physical intimacy means in a new relationship. I love your take on this – that the right people will be like, “Yay, we had sex – and now we can continue getting to know each other.”

As for your friends, it’s OK to ask them for time without significant others. Sometimes there should only be two wheels – you being the first. Also, reach out to single acquaintances who have more free Saturday nights. Make multigenerational connections. The circle of life, from my experience, involves people being free, then busy, then free again, then busy again, because of relationship, kids, caretaking for relatives, etc.

It doesn’t mean these anyone is a bad friend, but it helps to know a bunch of people in your own stage of life. I wound up hanging out with some younger friends when I was single in my mid-30s. Now those younger people are all in their 30s, and a lot of them are getting married. My older friends have all the time in the world. It sounds like it’s time to expand your group.

– Meredith

Readers? Memories from 29? Or is that you now? Share, please.

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