Updates: “Second Guessing” Responds

It’s time again for “Dear Wendy Updates,” a feature where people I’ve given advice to in the past let us know whether they followed the advice and how they’re doing now. Today we hear from “Second Guessing” who broke up with a boyfriend she wasn’t completely sure was “the one” when he told her he was going to turn down a great job in another city, near his family, to stay with her. She was worried maybe she broke up with him too soon and wondered whether she should give it another shot. She also wondered what “the basic ingredients in order to spend your life with someone” were. Keep reading to see whether she got back together with the ex.

Thanks for your response and, everyone, thanks for your comments. It’s been a little over six months since I broke up with my boyfriend; we didn’t come back together and I’m at a much better place now.

When I broke up, I knew it was the right thing to do, but, with everything that happened after (people telling us we were so cute together, feeling sad without him, having mixed thoughts and suggestions about what to do), I started doubting myself and felt guilty that maybe I could’ve tried harder. After writing to you and showing him your response, we talked about it and he said it couldn’t work because he felt I wasn’t the type of person who would push through in the face of difficulties, that I might just leave again. That actually made things worse, because then I tried to prove to him I wasn’t like that. When that failed, I then started dating someone else to get my mind off him, someone who was much more “compatible” with me, at least personality-wise. He was sweet, charming, and a really great guy, but after two months I realized that I wasn’t falling in love with him. I was still thinking about my ex, and it was also a time where we were getting along really well (still seeing each other as friends).

I think what ultimately happened (although it took me a while to realize), was that I was scared that I wouldn’t find someone else to love who would love me too. I have people in my family who are in their late 30s and still single, and all the ones who are married met their SOs relatively young (late teens to mid 20s), and there was a part of me that thought that I’d just blown my chance. But then something interesting happened: my ex met someone else. Someone whom I thought he’d actually be more compatible with than me, which made me realize that, if he could find someone better for him, so could I.

It sounds really silly when I say it now, but it helped me come to terms with the fact that we wouldn’t be coming back together, and, although I am now single, I feel ready to mingle. For the record, we’re still friends, which is great now that I’m over him. I think I’ll also try to put less pressure on my relationships, and just enjoy them for what they are, instead of trying to figure out everything right away.

Thanks for the update and best of luck to you! And remember: there’s no deadline for finding your right match/life partner. It’s not like once you hit 30 or 33 or 38, or whatever age you think of as “old,” that it’s over. Try not to compare your life trajectory to other people’s and you’ll be happier for it.


If you’re someone I’ve given advice to in the past, I’d love to hear from you, too. Email me at wendy@dearwendy.com with a link to the original post, and let me know whether you followed the advice and how you’re doing now.

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  1. Wendy’s response X10000 !

  2. tbrucemom says:

    I definitely think the LW needs to just enjoy dating and getting to know someone instead of trying to find “the one” with someone she was with 7 months and worrying about not falling in love after 2 months!

  3. I met my husband at 37. Married at 39.
    Love is for everyone…any age.

  4. Still single at 41, which sometimes is depressing – no, sad i guess, but I’m much happier now than I was with my ex where i felt I was “supposed” to stay with him because of my age (or aging). Keep the faith. i still do!

  5. I met my husband at 20 and we were married for 20+ tumultuous years. Very compatible in some ways and not in others. Ultimately, I couldn’t handle his money management or the midlife crisis and booted his butt. It still took us 6 years to divorce because he wouldn’t sign the papers.

    Long story short, at 41 I met the love of my love when he started hitting on me in our online writing group. He was much younger but the distance allowed us to get to know one another really well before we even started talking on the phone. Two years later he moved to California to be with me. That was nearly 18 years ago and all is well.

    You’re never too old to find love.

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