A year later, it's the same problem

Tuesday | October 10, 2023

Love Letters Dating

A year later, it’s the same problem

I wrote to you last year about a relationship I was in with a woman who wasn’t sure about meeting. She is working on the West Coast with her company right now and plans to retire at the end of the year back home. She lives in an entirely different state, and I live many states away from both places. When she’s home, we’re about a two-and-a-half-hour drive apart.

Anyway, you suggested I break off the relationship since she did not want to meet. Well, as you can tell … I didn’t break it off, lol! Now we have been talking for a year and a half. We have become somewhat closer, and I get the feeling she might be interested in seeing if I am worth the wait.

I am selling my home but still going to live in the same area I do now. I have asked her if she would like to meet me for a long weekend in Vegas after the house sale goes through. I told her to think about it before she answers, and that I would let her know if/when the sale is complete. I told her if she declined to meet me that it would not affect the relationship we have.

I believe we are both enjoying what we have, but I’m still not sure what to do. She sends me pictures of us together (it’s just pictures of me that I’ve sent her, with picture of her). Recently, she told me she has attention deficit disorder.

I’ll ask one more time: What is my best option? She is 70 and I am 69. I am really attracted to her and I feel she is starting to care more for me. I’m stuck! What do you think?

– Progress

Sometimes readers don’t like that my advice can be too … soft. I try to explain that I’m meeting letter writers where they are. If it’s clear to me that someone isn’t ready to hear “move on with your life,” I recommend a smaller next step.

I was hoping you’d break it off with that woman last year. That’s my hope all over again in 2023, but I understand that’s not what you want to consider after all this time.

With that in mind, a few thoughts:

Do not make any decisions about where to live based on this woman. It sounds like you’ll stay put, which is good.

Maybe there’s an easier trip than Vegas for a first big outing. What if you offered to meet her in a scenic and populated spot near the town where she lives? The person who’s been reluctant to see you in real life might be put off by the idea of many days in a hotel room.

Do not give this woman money from the house sale. Make no promises about what you’ll share.

Consider dating others while you wait to see what she’ll do next. Finding more people you like might be a challenge, but they’re out there – and local. There are apps, activities, and setups. A nice thing about dating apps is that new people join them all the time.

I’ll say it again, but if she doesn’t want to meet up anytime soon, consider what I advised last year. You seek companionship, but she isn’t offering that right now. She’s a pen pal, a crush, a fantasy. Even the photos are an art project. Maybe, this year, you’re ready for reality.

– Meredith

Readers? Advice the LW might follow?

Dating

Featured Comment

I’m your age and met my partner online. There are loads of women your age online, who will call, video chat, and meet you–and if they like you–have real sex, not cyber sex.

This pen pal is either a scam, or has no interest in a real relationship.

Either your online profile needs a lot of work (ask a family member or friend), or you are scared to meet because you have little relationship experience.

A therapist could help sort this out.

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