“Is It Wrong To Date Someone I Emotionally Cheated on My Late Husband With?”

Back in the 90s, when I was married, there was a guy I worked with whom I developed a crush on, and it lasted about six months. We went to lunch together, he made me mixed tapes, he bought me books, we talked a lot, etc., etc. I went to his apartment twice and to his office twice. We never had sex and our friendship was not romantic. But I know it was still wrong since I was married (10 years married at the time). We started pulling away from each other, and a month later I found out my friend’s sister had been dating him for a year. It is now twenty-eight years later and my husband has passed away. This guy and I have started texting. So my question is, would it be wrong to start dating him, considering the past? I am still in contact with my friend and her sister (the one who was dating him). — Ready to Date

When you say you aren’t sure about dating him, “considering the past,” I’m going to assume you’re thinking of the following issues:

1. The emotional cheating you did on your husband.

2. The emotional cheating this man did on his then-girlfriend of a year.

3. The connection you had and still have to the woman who was his then-girlfriend.

So, let’s consider the issues then.

1. While you were wrong to emotionally cheat on your husband for six months 28 years ago, he’s gone now and can no longer be hurt by your actions. If you feel too guilty to date someone who once posed a threat to your husband and your marriage, albeit unbeknownst to your husband (presumably), that’s something to think about. But if you don’t feel guilty — and I don’t see why you need to — then it doesn’t matter.

2. This guy not only emotionally cheated on his then-girlfriend for six months, but he also never told you that he was in a relationship. He deceived both of you. Does that mean he’s a bad person? Of course not. And it was so long ago anyway. BUT, it is something to keep in mind as you move forward. Can you trust him? Listen to your gut on that and go slowly until any fears are put to rest.

3. As for your connection/friendship with the sister of your friend who once dated this guy, it only matters if you feel like their relationship was significant enough and your friendship meaningful enough that she would feel hurt or offended by your dating him.

If you can address all of these issues and the idea of dating this man is still appealing, I say go for it. It’s not always easy to find someone you connect with, and maybe you can find that with this guy. If nothing else, you can reminisce about the days of mixed tapes with someone who remembers when you were young.

I’ve recently moved to a new city and quickly met a new guy. In three months, we moved rather quickly, becoming joined at the hip (and other parts). Friday-Sunday, along with some weeknights after work, became our time. We even took two trips, back to back, a couple months ago. One was to my former town, where my good friend left us her apartment. There, he met a few of my old friends and got a sense of my old city. I paid for us to travel there, but he took care of most of the trip.

Our next trip was to DC to catch his favorite band in concert (he missed them in our current city). He flew us up and took care of just about everything financially. After this trip, things became weird. He started responding to my texts/calls with short responses, if at all. Eventually, he began ignoring me all together.

This past week I’ve felt crazy replaying our time together, trying to figure out what happened. I’ve sent him a few “I don’t understand”, “What happened?” “Is it me?” and finally a “Well, it was fun while it lasted…” texts – each one taking a bit of soul as I watched my pride go down the drain.

The thing is, I’ve never been wined and dined by a guy before. I’m used to chipping in and sometimes being the “breadwinner” in my relationships, which was fine since most of my relationships were with guys still in school or just gaining their footing, as I was. So, I wasn’t with this guy for the money; I truly enjoyed our time together and have let him know.

Wendy, what could have happened? And how can I move on? I’m a bit shocked, because his rejection has come out of nowhere. — Dazed and Confused

His behavior is not a reflection of you and it is not about money. I’m not even convinced it’s a rejection in the traditional sense, though I appreciate that it looks and feels that way. Really, anything could have happened – maybe he was in another relationship and was cheating with you and got caught; maybe on your second back-to-back trip he realized he wasn’t ready for a serious relationship and sensed you were and he lacked the emotional maturity to actually discuss with you how he was feeling and chose to ghost you instead. These are just two ideas among many possible scenarios. None of the scenarios really matter much. What does matter is that this guy clearly isn’t “it” for you. Not only is he not “it,” but he clearly lacks common decency and even the most basic communication skills. Something obviously happened that made him decide not to continue a relationship with you and he wasn’t able to tell you it was over. That’s pretty pitiful.

His behavior is a clear reflection of his glaring flaws – flaws that make him an inappropriate choice in a partner; his behavior is NOT a reflection of you. I know you’re hurting now and your ego is bruised but try to see this as a gift. You dodged a bullet and it only cost you three months of your time – three months when you were new to town and didn’t have many other people to spend that time with anyway. Next time you meet someone, you may be a little slower to get to know him, and that’s ok. But I hope you will continue to open your heart to the possibilities out there. Nothing great and meaningful comes without some risk. This time, it didn’t work out for you the way you wanted. Next time, it just might.

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If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.


  1. LW2: Be grateful that he disappeared early. I dated someone like this for almost a year before he just…disappeared. When I finally confronted him (he’d invited me to fly to visit him), he refused to talk even when I asked. So I left and never saw him again. Somewhere in there I think he mumbled something about being ’emotionally stunted.’

    1. Years ago, a friend of mine moved in with her on/off boyfriend of five years. She traveled a lot for work. One time, she came home from a work trip to find he’d moved out without a word. That’s like the ultimate ghosting!

  2. LW2 – I’m sorry! It must really hurt to be ghosted after a few intense months. The way people end things with us can be more revealing of who they really are than the thoughtful or grand gestures they make when we’re dating. This guy is showing you that he’s emotionally immature and a poor communicator. All he had to do was send a low effort text along the lines of, “I’ve had a wonderful time getting to know you, but I don’t see this relationship going any farther.” He couldn’t even manage to do that. You move on by reminding yourself that this guy doesn’t meet your needs or standards. You now know exactly who he is.

    FWIW, I moved to my city alone and didn’t know anyone here. I very quickly jumped onto the dating apps. If I had a do-over, I would not have focused on dating at all while getting settled. It was already a high stress time, I didn’t have a routine established, and I had yet to build a support network. I think all of that meant I took some dating outcomes harder than I would’ve otherwise.

  3. LW2 this is classic narcissistic behavior. The love bombing and then the discard for seemingly no reason. I know because I experienced the same exact thing and was left feeling so confused. No doubt he will come back around at some point, they always do and at that point your job is to ignore him. In fact go ahead and block him right now. This has nothing to do with you. Read up on this type of behavior it will help you gain some understanding into what happened and how you can avoid it in the future.

    1. Ugh. Armchair diagnoses of narcissism are really “in” right now on the internet even though statistically, clinical narcissism isn’t that common. I’d say odds are higher that this guy is shady, selfish, and/or an asshole.

      I do agree with blocking him, though. It puts a barrier between LW and the texts she is sending that rob her of a tiny bit of dignity every time with the added benefit of never needing to know if this guy comes sniffing back around.

  4. Anonymousse says:

    For LW1: he lied to you all those years ago, and not just a small lie. It was a huge lie.
    I know you can do better than digging in the past for untrustworthy former cheating partners.

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