I found his messages to his ex

Contemplating a breakup? A crush? A divorce? A new beginning? What's on your mind? Send a letter to [email protected] or fill out this form.

I have been in a relationship for a year and a half, living together for six months. I am clear that my 58-year-old boyfriend is a flirt, but recently I learned that he has been private messaging a long-term ex via Facebook. He has told her he "thinks about her every day," he sends her old photos of them and makes comments about how much he likes that picture, and even went so far as to ask her to meet for lunch for "old time's sake."

For her part, she has ignored many messages but did answer some. She refused his lunch invitation. I see this as a complete betrayal; he does not, as they were only "friends" for the last five years. She is 81 years old.

Am I overthinking this, or am I spot on with my feelings? I feel he isn't trustworthy.

– I Deserve Better Than This

P.S. I found the messages, he wasn't forthcoming.


You're uncomfortable with his flirting. This other woman seems to be too.

At the very least, she's not very interested in giving him her time.

This could be about him reminiscing and taking a moment to appreciate his history with someone, but even if his intentions are innocent, your feelings should be part of the equation. He didn't explain much about what he wants from this ex right now. There was little empathy for your confusion.


But let's forget about this woman for the moment. The real headline of this letter is in your second second sentence. You say you know your boyfriend is a flirt – and you don't seem to like it. You "found" these messages because you knew what you were looking for. The vibes were already off.

You'll have to deal with the flirting, even if this woman isn't a threat. Can you handle that? Will you be tempted to check his phone again?

Honestly, a year and a half is a long time, and six months of living together is an investment. But if your relationship has led to this – you believing he can't be trusted – that says it all. Why stay?

– Meredith

Readers? Is this a deal-breaker? Could these messages be about friendship?