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Should I give him another chance?

‘I brought him to my cabin for a weekend. After the trip, photos surfaced of him kissing another woman.’

Love Letters

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Q. I’ve been a widow for almost four years. I told myself I would never date again, but because I was widowed at a young age, well before my 40s, I decided I would try. I have dated a small number of men; some were immediately big no’s for me and others became friends. One of those friends and I fell in love after about six months.

He’s wonderful, we never fight ... but he’s done hurtful things on three separate occasions. The first was after I brought him to my cabin for a weekend. After the trip, photos surfaced of him kissing another woman. He said that despite us taking the trip, we weren’t exclusive at the time. I thought it was unspoken under the circumstances.


The second was when we ended a call but he forgot to push end on his phone so I heard an entire conversation where he belittled me, said I wasn’t his type, but said I gave him the best experience of his life (referencing something sexual). He basically said he wasn’t interested because I wasn’t 22. I stopped taking his calls after that ... until he started to make that hard because he was sending me flowers and coming to work with gifts a lot. We reconciled, and for months it was beautiful.

On Christmas 2021 he invited me to his family’s home. I had a gut feeling and did something I never do — I checked his phone. I found countless messages that included sexting. He was telling a woman he was with me, but wanted to have sex with her. Other messages were to women he’s had more significant relationships with, including one who said she had a miscarriage. He was having sex with her while in a relationship with me.


I will not toot my horn but I am more attractive than him and these women.

After that final straw, he apologized publicly on social media, called my father and apologized, has sent countless flowers because losing me “made him realize he has struck gold” with me. Can I trust him? Should I even consider it?


A. I don’t see any reason to stay with this man.

It does sound like the two of you have good sexual chemistry, but that’s not enough. Your gut told you he was lying, and it was worse than you feared.

There are other people out there looking for love. Some would be very excited to find a 40-something who likes intimacy of all kinds — and has a cabin!

And maybe it’s my allergies talking, but I have no idea why flowers make up for betrayals. It sounds like he has the florist on speed dial, which tells you a lot about how often he messes up. He doesn’t respond to these mistakes by making real changes. Also, “coming to work with gifts” is intrusive, not romantic. He’s not thinking about boundaries at all.

He’s shown you who he is, so call this what it was — an experience that taught you more about what you need from another partner. You’ve learned about instincts, conversations about exclusivity, and so much more. If you need a break after this relationship, that’s OK. You can date ... or wait. Your gut seems to know what’s up, so trust it.




You say that’s he’s only done hurtful things on three separate occasions. You should consider that these are only the three things you know about. Don’t fall for the flowers bit — end it now.


Three strikes and you’re out baby!


There is literally no reason to trust him, and therefore no reason to stay with him. If you consider flowers a worthwhile price for sacrificing your dignity, you might need therapy.


“Can I trust him? Should I even consider it?” I’m sad that you’re even asking this. You should have been done after example #2 after you heard him belittling you and saying crass things about you to another person. That was absolutely appalling and no amount of apologies should have had you stay in a relationship after that.


“When someone shows you who they are, believe them the first time.” — Maya Angelou


Send your own relationship and dating questions to loveletters@globe.com. Catch new episodes of Meredith Goldstein’s “Love Letters” podcast at loveletters.show or wherever you listen to podcasts. Column and comments are edited and reprinted from boston.com/loveletters.