Will he repeat his mistakes?

Good morning. Thanks to everyone who entered the "Becky Shaw" contest. I may give away some more tickets to another performance later this week. We'll consider Friday's entries, so no need to enter a second time. Details to come. For the record, the play is very Love Letters-esque. Lots of problems. No easy solutions. Angst all around. Today's problem is "two-pronged." I hate problems that have more than one prong.
Hi Mere, This letter comes to you from a woman "of a certain age" who has been married, divorced, cohabitated, and dated. Whew! I've learned everything the hard way in relationships with guys, as many of us do. Recently I met a man online who gets me going on all cylinders: we interact beautifully intellectually, in humor, enjoy music trivia, have an attraction to each other; we talk for hours, you know, all the early relationship stuff that makes one's day brighter. Here's the two-pronged problem: he revealed to me that he cheated on his wife and it ended their marriage. His reason for cheating was because of a sexual "dry spell" of six months. When he told me about this, it was as if all the air was sucked out of the room: I was saddened and disappointed. The revelation had such intensity because my husband had cheated on me and that's how my marriage also ended, via infidelity. I told new guy that I wasn't sure I could continue in this relationship and needed a few days to think. There's another factor here as well: even though we are the same age (early 50s), I am the oldest woman he's ever dated. This fact makes me feel uncomfortable and frankly, unattractive, at least in this scenario. We do have tons in common and click well ... but ...?

– Baffled, Boxford

Good question, Baffled. He screwed up his marriage, but that doesn't mean he'd do it again. My big question is – Is he self-aware about his past? Does he have regrets? When he told you that he cheated because of this "dry spell," did he acknowledge that it was a mistake? Did he learn from his experiences? If this guy moves from one relationship to the next without evolving, experiencing remorse, or learning about himself, he's not worth your time. But if he seems to have used his past experiences to become a more courageous partner, he's worth getting to know. And the same goes for the "you're the oldest person I've dated" thing. When he told you that you're his most, um, senior significant other, did he seem happy to date a peer? Was he conscious of the fact that the comment might have hurt your feelings or made you insecure? People mess up all the time in relationships. It's up to you (and your gut) to decide whether this guy is thoughtful or thoughtless about those mistakes. Past screw-ups and bad patterns are forgivable. But thoughtlessness isn't, especially when you're in your 50s. Do you think he has learned from his mistakes? Readers? What's with this guy? Should she give him a chance? Is it weird that she's the oldest person he’s ever dated? Will he cheat again? Is she overreacting about his past? Thoughts.

– Meredith