Should He Give Him Another Chance?

August 12th, 2016

Casual sex, NEW!, Rebound, Sex


Name: Jordan
Question: Hey Moxie,

First off, I hope that all is going well with the blogging break. I could use some advice from you and/or your crew.

5 characters:
1. Me
2. Jay (way out of my league, met through the following guys, went on a date)
3. John (friend of 2 years, he’s closest with everyone)
4. Jack (cool acquaintance of 2 years)
5. Joe (cool acquaintance of 2 years)

I had some scheduling issues on my end, so the date was my treat. Jay and I have what I thought was a great date, except for a few red flags. He’s recently divorced, new in town, and isn’t financially comfortable yet. To me, that says casual, which i THINK is fine. He also said that he likes when guys take charge and order for him. On my end, I said that all I need in dating is space and understanding in dating. Back to the date.

After a few glasses of wine and not much food, we go back to his place and have sex. While it was a LOT of fun, I wish I hadn’t drank so much. Afterward, he insists on meeting [up with] Joe/Jack, which seemed fine. There’s no way I wanted to go to bed yet.

After that, boom. He offers me a drink and says nothing else to me. Jay’s arm and arm and laughing it up with Jack. They were borderline flirtatious with each other the whole time. Joe tries to keep getting me to dance with him/distract me and I humor him for a little.

Honestly, I felt like the fourth wheel/dismissed so I left without saying anything. He asked me if I got home ok the next day and I didn’t respond.

The next day, Jack calls John (the one we all know) and fills him on everything, explaining that he feels bad. He says that he didn’t know that Jay was showing up with anyone, didn’t know that Jay and I went on a date that night until much later that night and that he was really drunk. Do I get a call or apology? Nope. Did I hear from or talk to anyone? No.

10 days later, Jay messages me believing that I’m mad, apologizes, wants to talk about it, says that he can be really clueless, and asks for forgiveness/ to be friends (all in one letter. Odd?). I tell him that I felt like we weren’t a good fit and wished him the best.

For the sake of group politics, I pledged to go along to get along. Ever since then, Jay/Jack are only pleasant to me in group settings. If I see them together or on their own, not so much. It’s really just spurring some sensitivity and major trust issues for me. And it hurts like hell that I have to fake getting along with them so that I don’t look defeated or bitter (both of which I feel).


A lot of my friends have said, “Well, maybe he had too much to drink. You should consider that and give him another chance.” Would you say that there is validity to that? Was I expecting too much in a casual situation? Is group politics even worth it anymore? My gut says no to all of these questions, but I could use some objectivity.

I know it’s long, but thanks to you and your commenters in advance.
Age: 30

Admittedly, this one is a bit hard to follow.  All I had to hear was “newly separated” and “new in town” for me to tell you to keep this guy at a distance. If he was flirting with another guy in front of you right after having sex with you, that’s horrible. I wouldn’t want to hang out with someone who treated me that disrespectfully either.

Here’s what this all boils down to: you’re hurt because for Jay this was a one nighter and for you it was a bit more than that. You’re also bothered because the minute you and he got around other guys, he blew you off. That’s totally understandable. But I think that hurt might be coloring your perception a bit. I also think you might be bringing some “stuff” to the table that has nothing to do with Jay. A lot of people like to say that things are different with gay men or women, that casual sex is more acceptable or prevalent, etc. That’s not how any of this works. Feelings are feelings.  Our emotions are not predicated or dictated by our sexual orientation.

You mention Jay was way out of your league, that you paid,  and that you had some drinks and immediately went back to his place for sex. Then you continue to make excuses for this guy when – after you have sex – he wants to go out and hang out with his guy friends. Gay or straight, this is a classless move. Sure, maybe once he knew you a bit he could make a suggestion like that, but not on the first date.  There’s a boat load of insecurity going on here with you that borders on trying too hard.

Jay was just the trigger. What you’re feeling has always been there underneath the surface. You went out with a guy you knew was out of your league. First red flag. Then he tells you about how he’s newly single. Second red flag. Then you got tipsy and went home with him and – immediately after having sex – he wants to go out. THIRD RED FLAG SO BIG YOU’D HAVE TO BE BLIND NOT TO SEE IT.  He’s calling you up to mend fences because your friends probably told him they didn’t appreciate that he treated you poorly. Good. That means you have friends that care about you.

So, no, don’t cut off all ties here. Suck it up and be pleasant and cordial to Jay.  No, you should not give him another chance. Meanwhile, take the time to do perform some introspection and deal with your insecurities and triggers.




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3 Responses to “Should He Give Him Another Chance?”

  1. coffeestop Says:

    Newly divorced and not financially comfortable yet. OP also says he is way out of the league, flirting with other people seemed to have happened. This sounds like too mcuh drama/baggage/complications.

  2. Bostonette Says:

    Op seems like a logical guy willing to put it aside for a guy who is “not in his league” …actually I agree…he’s LOWER. Not because he’s a bad person, but because he’s in a place in his life where he’s not thinking about others. Maybe that’s where he needs to be right now, but you don’t need to go there with him. You sound cool, hang in there and if you’re pissed at the situation, trust yourself that this isn’t what you want in a person and move on. Good luck.

  3. SB Says:

    First off: this guy is a jerk. He treated you terribly, as Moxie so rightly said. Do not give him another chance (whatever that means, as it doesn’t seem he’s offering that. You must mean a fair chance as friends? Whatever it means: NO).

    Be cordial/civil to him whenever you see him, whether that’s in the group or alone or when it’s just you and he and his current fling/boytoy. Regardless of how he treats you, keep it classy. Don’t get any emotions involved hoping for actual friendship, any civility or social consideration from him or Jack (is it?), or certainly anything more. You are doing this for yourself.

    Lastly, move on. Continue to invest in and tend to your real friendships with the rest of the group, and expand your circle and dating prospects. Continue to date, in your league, with an open mind for a good person.
    Also, seek therapy. I don’t see you as broken somehow. I believe everyone needs it, especially after something triggers stuff in you like this. If you miss big red flags, or notice disturbing patterns in your dating life, or even if you are just feeling off-balance by this guy’s behavior, therapy will help you sort all of that out and unpack some stuff from your past that will enable you to grow and come into your own. All of that will only help you – in dating and in the rest of your life.

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