Getting past a first date at 40

Thursday | December 14, 2023

Love Letters Dating

Getting past a first date at 40

I’m seeking letters about long-term relationship issues, dating, marriage, divorce, etc. What’s on your mind about your relationship life?

Submit an anonymous letter here or email
[email protected].

Meredith,

I am struggling with my love life this year.

Every recent date has been fun, but they don’t lead to a second.

I am 40 years old. I consider myself kind, quirky, funny, and compassionate. And fairly good looking. I have great qualities to offer in a relationship.

But I haven’t had emotional or physical intimacy for years. It’s hurting my mental health, and emotions. As they say, “I have needs.”

Separately, I am in love with my dear friend. She is in an incredible, smart, funny woman. She is a one-of-a-kind catch. We have discussed my feelings; she does not have them. But she has been a devoted and loyal friend, especially when she came to my hospital bed after major surgery.

How do I break my unsuccessful dating life? How do I cope with my feelings for my friend?

-Lonely Aging Suburban Guy

If you have a good community outside of this dear friend, it might be best to take space from her.

It’s possible the friendship isn’t affecting how you bond with people on first dates … but I think it might have a lot to do with why you don’t click with anyone new.

I remember going on a date after a breakup and being frustrated that I couldn’t connect with the person in front of me. I thought it was a lack of chemistry, shared humor, etc., but frankly, had the new guy been the hottest and funniest person on the planet, I might not have noticed. My brain was still in my last relationship. It’s so hard to notice anything when your mind is elsewhere.

You might have to separate yourself from your friend, grieve the end of this era of your relationship, and reboot your life with room for someone new. Loneliness is awful, but it’s an extra kind of bad when you pair it with constant longing. It would be a gift to feel like you could meet someone any day now – which is the truth! It would be nice to know that nothing is in the way.

That’s my unpleasant advice – and I understand it’s difficult to take, because who wants to lose a close friend? But sometimes being alone – as opposed to being trapped in an unrequited love situation – feels less lonely.

Give yourself the chance to meet someone and see them clearly.

– Meredith

Readers? Any way to do this while keeping the friendship? Pep talk, please?

Dating Dating fatigue Health 🖤 Unrequited Love

Featured Comment

“For starters, you need to put some distance between you and your female fried. Pining over someone who doesn’t feel the same way is keeping you from connecting to others.

You don’t provide a lot of detail about your dating life, but it’s a good sign that you’ve been going on a lot of dates. If like the person you’re with at the end, a sure way to get to date two is at the end of the date, say to her “this was fun, would you like to go out again” and then make a plan.”

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