“Should I Give Him A Second Chance?”

I was in a relationship with a man (we will call him Greg) for over 2-1/2 years. The relationship was great for the first year. After that it was fraught with issues — mostly stemming from the fact that Greg had one foot in his prior marriage. Without going into detail, Greg was divorced. He lived at home with his ex-wife (we will call her Sheila) for the sake of co-patenting their children who have autism. However, their relationship was much closer than that of co-parents (more of a best friend situation where Greg would discuss our problems with Shiela. I felt that was inappropriate and we fought about it a lot).

I was as patient and understanding as I could be, but when my feelings developed into something deep and real and I wanted a genuine life with Greg, he started shutting down and backing away from me. Eventually things got so bad that I ended our relationship.

Fast forward to a month after my breakup with Greg: I found out Greg had been spending an inordinate amount of time with a single female “friend” (we will call her Tosha) toward the end of our relationship. To this day, I have no real proof that anything crossed the physical cheating line, but some definite boundaries were crossed. Within days of our relationship ending, Greg and Tosha were in a relationship (something I would not discover until almost five weeks later).

When Greg and Tosha were very early into their relationship (Greg assures me it was before they had the official talk), Greg was intimate with both me and Tosha. After I found out about the situation and confronted him about it, Greg was very back and forth about his feelings regarding me and Tosha. When I discovered the full story of everything that happened, I cut off all contact. It took me several months to get back to a happy and healthy place.

After three months of being together, Tosha and Greg broke up. Greg is in the process of moving out of the home with Shiela. He really seems to have grown up. He turned up at my apartment one night a few weeks after the breakup with Tosha and we talked, and we have had several conversations since.

Greg seems more attentive and understanding. He has taken responsibility for all the damage he caused in our relationship. Greg is present when we spend time together in public (something he was terrible at when we were last together). Everything seems perfect, but something in my gut is telling me it’s too good to be true.

Greg and I have had a couple of conversations about getting back together. I seriously considered taking him back, but somewhere in the latest conversation Greg mentioned that Tosha had gotten a hotel room for them to spend the night together this past Thursday. I believe he told me so there would be no secrets between us. Greg didn’t meet up with Tosha, didn’t respond to her request in any way, and spent Thursday evening at dinner and talking with me. I knew they still talked and I understood it, even if I didn’t like it.

Honestly, if Greg had really closed the relationship properly, Tosha would not consider asking such a thing of him. It bothers me a lot that Tosha still thinks they can have a physical relationship. Greg tells me he has had no physical contact with Tosha since he and Tosha split up and the only reason he hasn’t completely shut the door with her is because he’s afraid of how she will react. Greg tells me he doesn’t hate Tosha, but he doesn’t want to be with her.

I understand Greg doesn’t want to confront Tosha and hurt her feelings any more than he has. But Greg constantly seems to make this mistake over and over — never truly letting things go and moving on.

Last night Greg asked me to make our relationship official. I’m not seeing anyone else and part of me wants to do it. I love Greg more than I’ve loved anyone. But he hurt me so badly that I can’t put myself in the same situation as before.

Am I wrong to tell Greg that he needs to cut Tosha out of his life and sort out his feelings alone regarding her and me before we can get involved again? Obviously, I don’t want to control Greg’s life or his friends, but given the situation between all of us, I think it’s the only way I can protect myself.

So, should I take him back or not? And if so, are my conditions unreasonable? — Second Chance?

You say you don’t want to put yourself in the same position you were in before, but it sounds like the only thing that has truly changed with Greg is that, instead of having one ex he still has unfinished business with, he now has two. The red flags are flapping in the wind, lady; stop ignoring them and MOA. If you got hurt touching one burner, why on earth would you wave your hands around two burners going strong?!


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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. Seems like Greg can’t be alone and likes to take up with someone new before he’s quite finished breaking up with someone old, and his method of “not hurting feelings” looks a lot like keeping all his options open and multiple women dangling on his string. Look, it’s been lousy at least as long as it was good. That’s a 50% suck rate. I think you can do better – don’t you? Good luck!

  2. Wow, he sounds like a dream boat. Ok look, regardless of the reason he lived with his ex wife, you surely couldn’t think that would be workable in your relationship with him. Apparently you did, but how or why I cannot even begin to guess. He very likely cheated on you with Tosha and continues to keep her on the line for some reason (sex I would guess, or he really hasn’t broken up with her at all). See what is right in front of you.

    I mean, SHOCKING, that a man is saying what he knows you want to hear to be back with you! That has never been done!

  3. Greg was cheating on you with Tosha and cheating on Tosha with you.

    1. Avatar photo juliecatharine says:

      I doubt anything has changed on that front.

  4. I wonder if some areas have so few single men that this guy was able to keep 3 women dangling (his ex wife, LW, and Tosha)

    LW, what exactly has changed since you guys broke up that you would consider a relationship again ?
    He is still great friends with his wife and now there is a Tosha in the picture.

  5. Northern Star says:

    “But Greg constantly seems to make this mistake over and over…”

    Poor, hapless, accident-prone Greg. He keeps tripping and sticking his dick in other women besides his girlfriend. What a butterfingers!

  6. Avatar photo Skyblossom says:

    Do you think you will ever trust him? Without trust the relationship is already over no matter how long you drag it out and no matter how much you love him.

  7. He’s a player. You are the side chick, and the side side chick. Why are you doing this to yourself? And he should be spending more time with his two (or maybe more) children who have autism (if that’s even true). And he’s so great that you want to take that on? Get yourself checked for STDs because this is just the tip of the iceberg.

  8. Avatar photo SavannahAnna says:

    I agree with Oracle that, if he does truly have at least 2 children with autism (do you know that to be true, LW?), he needs to be spending a lot of time with them. What happened to the “co-parenting” that you mentioned earlier? Instead, it’s sounding like a ton of drama between him and at least 3 adult women. The guy isn’t a prize.

  9. dinoceros says:

    I know you WANT to think he’s changed because you want to be with him, but people don’t usually change this drastically this quickly. Also, the things you are listing as exciting changes are really the bare minimum. He pays attention to you in public? He took “responsibility” (whatever that means) for the things he did wrong? OK, and?

    It’s not difficult to be attentive or to say that something was your fault and apologize. In fact, those are easy enough things that you can do them when you are suddenly single and want to get your old GF back! Imagine that.

    Your relationship was pretty crappy. He cheated on you in one form or another. He apparently paid you no attention. He had a lack of boundaries with his ex to where he talked about your relationship with her. You’re acting like he’s some holy grail and you’ve just GOT to have him. Seriously? THAT is what you’re obsessing over? Move on.

  10. Oh, I know guys like this. Charming, attractive, really good at saying the right thing when they want to court you or get you back after you’ve gotten sick of their behavior and left them. Also, not remotely monogamous, and will aim that charm at the next shiny object when things start to get routine with you.

    You want a monogamous relationship. You’re not going to have one with Greg.

  11. golfer.gal says:

    Jesus christ. Aim higher

  12. Bittergaymark says:

    Why? Why would you even bother?

  13. allathian says:

    MOA. No need to give him the benefit of the doubt. Why should you let him hurt you again? Because he will, no matter how much he says he’s changed.

  14. Scarlet A says:

    Every time I read “should I take him back/give him another chance”, my gut is like NO YOU LEFT HIM FOR A REASON and to be honest that instinct has never been wrong.

  15. Calligirl says:

    Draw a line in the sand under this lot and move on. You deserve better than this.

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