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Dating in Boston has been rough

I have tried to be open-minded...

Love Letters

Love Letters

Q. 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 fifth, seventh, or ninth 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.



A. 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 in this letter makes me think there’s an unusual problem here.


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 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 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, 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.

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.




Don’t listen to people who aren’t on the dates with you. There’s no one way to go about dating. Go with the flow, date many types of people, treat each experience uniquely, don’t prejudge, and have fun. Also, live your life like you MIGHT end up alone. Structure your happiness so that you do not need a relationship to validate your existence. That way if you do end up alone you will be OK.


If you want to use dating apps for hookups then that’s fine, but you’re trying to get a relationship. It’s not going to hurt you to just wait. You can be both sexual and discerning.


If the apps aren’t working for you, try something different. Start with meetups. That’s how our nerdy introverted genius daughter found her nerdy introverted genius husband. Married for eight years and very happy.


Send your own relationship and dating questions to or fill out this form. Catch new episodes of Meredith Goldstein’s “Love Letters” podcast at or wherever you listen to podcasts. Column and comments are edited and reprinted from

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