We’re flirting, but only on Facebook

Q.

I need help navigating a new/renewed relationship where we are communicating almost solely by Facebook Messenger. Before your alarm bells go off that I am getting trolled, I do know him.

We dated when I was in high school and he was in college. He went off to fulfill his obligation to the military, then I went off to college. We had a close mutual friend with whom I also lost touch. From time to time, I would look for them. 

I was bored a few weeks ago and started looking again. I found his profile on Facebook, so I messaged him. He responded immediately saying he remembered me. I should add that I am now late 60s and he is early 70s. Ironically, we both ended up in New England and are about three hours away. He is retired. I still work full-time for myself.

The problem is that other than a couple of phone calls using Facebook messenger, we only communicate by messaging. We have been messaging every day and a lot in the evening. In addition to the nuances that are lost through this type of communication, when he unexpectedly goes silent for a couple of hours in the evening, I get concerned that something has gone awry.

I flirt and tease him a lot. He has said he is very grateful that I am back in his life. I think we both are hoping that this will turn into an actual relationship. I can be pretty insecure about relationships. He has been married before. I have not been in a relationship in decades.

We have agreed that at some point we want to meet in person. I am nervous about that for all of the usual reasons, but also because I need to lose weight. Meantime, I am trying to figure out how to navigate communication.

Help with all of this please.

– I Used to be Seventeen

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A.

See each other in person as soon as possible. That’s the advice. Is there any reason to delay?

You say you want to lose weight, so maybe you’re postponing a meetup until you get into a specific kind of shape, but … can you be kinder to yourself? I assume this man has seen pictures of you online. Doesn’t he know who he’s talking to?

It’s lovey to be in touch, but it would be easier to assess possibilities if you shared a meal. You could offer to drive to see him for dinner, or meet halfway. Make it happen within the next few weeks.

Remember, he’s probably nervous, too. Everybody’s older and different.

If dinner is good, you can discuss better ways to communicate (more phone calls, other platforms, etc.).

I wouldn’t be worried about a lack of relationship experience, by the way. Sure, it’s been decades, but the skills come back. The only real goal is to get to know another human and see where it goes.

Just show up and have fun.

– Meredith

Readers? How long would you keep a flirty pen pal before expecting to see them? Thoughts on prioritizing self-improvement before you give yourself the chance to see someone you like? What if he says no to dinner – or wants to delay?

Is there something on your mind about a relationship in your life? A friendship? A crush? A spouse? Send your own question. Help others wondering the same thing. Use the form – or email [email protected].

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