I Cheated At the Beach

Empathy. (I know, I know, this one's tough.)


I'm a 20-something guy in a long relationship. I can see myself being with her forever, and I bought an engagement ring a couple months ago.

Now comes the hard part. I recently went to the beach for a bachelor party with a group of close friends. This was a week for us to forget, cut loose, and live like we did when we were in college.

I am generally an outgoing guy that will talk to just about anyone. One night at a bar, I started talking to a very attractive girl, and I could immediately tell she was into me. I, of course, did not mention my girlfriend. Nothing beyond conversation happened that first night, but when I got back to our house that night, I could not stop thinking about this girl I just met.

Fast forward two nights and I saw her again. We talked again, and had some drinks. I asked if she wanted to go for a walk on the beach. She did and very shortly into our walk/conversation, I kissed her. After making out for some time (maybe 30 minutes), I walked her back to her place and she invited me in, but I did decline, saying how it was late. I saw her every night for the rest of the trip, and every night we would have drunk make-out sessions and talk and joke and have a good time together. I was torn because I have this serious girlfriend back home, but I could feel myself falling for this girl, and very quickly. I even bought protection -- just in case this "vacation romance" were to progress.

On the last night of our trip, she and her friends came to the house we were renting and she threw herself at me. I told her I felt sick and had to go.

She and I have since exchanged a couple text messages back and forth, but nothing scandalous. I have thought several times to go and visit her to see if there is truly a big enough spark there for me to run away from my current situation.

I know what I did was not right, and I have not told my girlfriend about any of my indiscretions. Since I came back home, sex with my girlfriend has not been the same, as I am racked with guilt. I am constantly thinking of this woman and wondering what a life with her would be like.

I am happy with my girlfriend and love her. But, if I am having these doubts, that can't be a good sign for my existing relationship, right? If I tell her what happened, I am afraid I will lose her. Should I tell my girlfriend? Should I go on a trip to see this woman again? Should I delete her from my phone and cut off all contact? Am I a total jerk for (1) doing this and (2) now debating leaving a good situation?? Help!

– Heart Robbed on the Shore, Boston

Tell your girlfriend. You might lose her, but at least you won't be lying to her anymore.

You're having serious doubts about your long-term relationship. You're actually wondering whether you might be happier with a woman you met at the beach. You're a guilty mess.

My advice is to tell her everything. Like, everything. Tell her that you've been planning a proposal. Tell her that you regressed as soon as you set foot on the sand. Tell her that you spent your vacation week pretending to be a younger, single version of yourself. Tell her that you couldn't quite go through with the cheat, at least not all the way. Then discuss.

She might kick you out. She might be a friend. She might tell you about her own fears and concerns. Or maybe she'll just yell. Regardless, you can't pretend this didn't happen, and if you were her, wouldn't you want to know?

Yes, you're a jerk for doing this, but you're not a jerk for questioning what this means about your relationship. This cheat is now a part of your history. Your girlfriend needs to be part of the discussion.

Readers? Should he propose? Does he have to confess? Should he go see this other woman? Was this just a panic move because he's about to propose? Would you want to know if you were the girlfriend? Should he tell her about the ring? Help.

– Meredith