Never Trust a Man Who Met His Ex In a Threeway

January 7th, 2017

NEW!, Women On Top, womne on top


When he told me he’d met his most recent ex-girlfriend via a threeway with the girlfriend before that, and that those two were friends, I should have known this guy was kind of a mess. The second girlfriend had problems with the first girlfriend and the first girlfriend was still heavily in the picture and so that gave the second ex-girlfrienf the sads. I heard all about it by the second time we hung out. Apparently the first girlfriend totally approved of the second girlfriend and encouraged the pairing. Because, of course.

Of course your second girlfriend didn’t like the first girlfriend. You date the ex of a friend or the friend of an ex and you’re a piece of shit. Period. End of. You complain about said friend whose ex you’re now dating, boo hoo. You brought that on yourself.

I mean, who puts themselves in the eye of that kind of storm? The ex of your friend? The friend of your ex-girlfriend? That you had a threeway with? So basically, she sat on your face before you two ever had an official first date? Oh, and your previous girlfriend that orchestrated the threeway is still your friend? Oh, and that first ex is someone you consider your “best friend?” Oh…OH…wait….and you have pictures of yourself with both of these women ON YOUR DATING PROFILE? (Dude, seriously. That was such an easy catch.)


I think it’s safe to say I got what I deserved.

Here’s how it started: Michael and I met on OKCupid back in November. Our first conversation knocked my socks off in that he wasn’t your typical OKC creeper dropping sexual innuendo every chance he got. He was normal. And interesting. And smart. We met up and talked for three hours, never running out of things to say. I won’t be cliche and say we had this amazing connection and chemistry because we didn’t. There was no flirting at all. So, the next day, I sent him an email saying thank you for drinks and that I didn’t sense a romantic spark but thought we’d be great friends.

I’ll stop here and say I’m an idiot. I found him attractive. I totally would have gone out with him again. I didn’t communicate my thought to him properly. What I meant to say was that I didn’t get the sense from him that there was a romantic spark.

He replies and says he agrees and that he wants to stay in touch. Now, how many of us have been in that situation and done the “let’s be friends thing”?

*Raises hand*


So I don’t respond because I think he’s just being polite. The next day I get a message from him with his phone number. “Text me whenever!” I respond with my number. A few days later he sends me a text “just to check in” and says we need to meet for a drink. Cool. Let’s do that, I say. Then I start to wonder if maybe I jumped the gun with my misguided “I didn’t sense a spark” email. (For those playing at home, I TOTALLY JUMPED THE GUN.) So, a few nights later, I text him and say:


To which he replied:


Can anybody decipher this? Anybody at all? He’s kind of circular here, yes? I respond and say that I get what he’s saying. (I DIDN’T. AT ALL!) No response. A week later I send him an email and say that if he just wanted to be friends all along, he should have said that. I asked him not to respond. Why? Because I didn’t want another word salad put in a blender explanation.

About a month later I message him. We talk. I ask him to meet for a drink that night. He says he can’t because he has a friend in town, but asked me if we could meet two nights later. Sure. Not a problem. So we meet. And again we have a great time. He brings up the fact that I said I’d be in the city for Christmas and that – if I wanted- we could hang out. Sure, I say. I’d like that. “Definitely,” he says. “I’m I’m around we’ll hang out.” Suddenly he wasn’t sure if he was going to be around. At that I assume he’s just being kind by inviting me to hang.

Two weeks go by and I don’t reach out to him. Christmas day comes and he sends me a text.

“Merry Christmas!” the message read.

“Same to you. Happy Hanukkah!”


Then…crickets. When he doesn’t follow that text up with anything concerning his invitation to hang out, I assume he’s blowing me off. I don’t respond. The next day I realize that – oh wait – maybe I was supposed to respond to that text. Not wanting him to think I blew him off, I texted him saying I thought it was weird that he messaged me on Christmas but didn’t bring up getting together.

“Umm, I thought the same thing. When you didn’t respond I assumed you made other plans.”

Ok. Fair enough. I suggest we meet the next night, a few days before my birthday. “Definitely!” he says. We meet up again, things are great. At one point he tells me I have chocolate on the corner of my mouth and reaches over to dab it away. Okay. Not something I typically do with my friends, but okay.

My birthday comes around and he sends me a text wishing me happy birthday. Very sweet. A week goes by. I hear about the mass shooting in Ft. Lauderdale and panic. Michael was coming home from Ft. Lauderdale yesterday. I send him a text asking if he’s ok. Then I wait.Finally he texts me. He was on the runway when the shooting began. I tell him I’m relieved. But in that moment I realized that this whole grey area thing wasn’t working for me. The fact that I was so upset waiting to hear back from him meant I liked this guy. If I spent more time with him, I would develop deeper feelings. Like I said, the fact that he dated his ex-girlfriend’s “friend” could be an indicator that he very well might be an asshole, depending on how close these two women were. If he coudl do that to someone he loved (depending on the situation) then imagine the teeth-kicking he could give me. Soooo, I bit the bullet and sent him this text today:


I don’t want to be angry, BUT……..

Come on. COME. THE FUCK. ON. He had to know he was sending mixed signals, right? Or was he not sending mixed signals at all and I’m just an idiot? Are my antennae so broken that I misinterpreted all of this?

He’d recently moved here from Boston. I couldn’t tell if he had much of a life here or not. I think I was the Friend Side Chick. Like, he had his main friends and then there were the people he hung out with when he wasn’t hanging out with them. He genuinely liked me as a person. I don’t question that. He probably just wasn’t attracted to me. It happens. Not his fault.

Here’s the thing: I’m glad I know. I don’t regret putting it out there so bluntly. It had to be said. Of course, the wine I’m drinking probably helps numb the pain. :) Kidding.


But the thing is: I still don’t think he’s a bad guy. He’s just a really bad dater. Like, he doesn’t seem to know basic dating etiquette. If you’re just interested in being friends, don’t pay the bill. (I once offered to pay the tip and he rejected my offer. “Next time,” he said. “But I probably won’t let you pay then, either.”) Don’t invade their personal space and wipe their mouths, you freak. (J/K!). Don’t invite them to hang out, period. Just walk away until a reasonable time has passed. Then try to be friends. His messiness could be because he’s a serial monogamist who has never been single for any significant period of time. Seriously, the guy has been in a relationship since he was 25 years old. Married and divorced by 33, then Ex number 1 for 6.5 years, then Ex number 2 for 1.5. He just turned 42. That doesn’t leave a lot of time for experience gathering. Or introspection.This guy was one continuous rookie move after another.

Keep in mind: we’ve never taken things to a physical place. He could have been that asshole who sleeps with women knowing he doesn’t want anything from them. He wasn’t that guy. He’s a guy who doesn’t know how to be anything but a boyfriend. Or he’s just a guy who needs women to like him so he tries too hard. He’s like that SNL character Caveman Lawyer. He’s single after a long stretch of being in a relationship and confused by our mystical world.


What say you? (This should be fun.)

PS…he gave me permission to write about him.

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25 Responses to “Never Trust a Man Who Met His Ex In a Threeway”

  1. michelle Says:

    He’s a mess. I knew when you told us that his ex-girlfriend was the friend of his other ex-girlfriend and that he posted pictures of both of them on his dating profile that he was a loser.

    Hot debate. What do you think? Thumb up 9 Thumb down 2


  2. Beta Male Says:

    He texted, you responded; you texted, he responded. He said, he just wanted to be friends; you said, you don’t do that. At any given moment you could have just disengage the texting, yet you continued to text back and forth. At the moment he said he just wanted to be friends and you told him you don’t do that you should have said goodbye.

    Is he a hot mess? I don’t know but I do agree with your assessment in the end but if he stated he just wanted to be friends and you continued to engage him after that at the very minimum he’s going to assume that you want to be friends.

    Well-loved. Like or Dislike: Thumb up 28 Thumb down 2


  3. Bree Says:

    I’m baffled. I figured Michael wasn’t interested in a relationship, but I thought he was taking it slow towards casual sex, making sure you weren’t going to be someone who’d want more than that. Maybe he concluded that you are, and that’s why he’s NOW saying strictly platonic. It doesn’t make sense otherwise, as the vast majority of straight men have no use for women as real friends and don’t go online looking for friendship. He just didn’t want to be an asshole, sleeping with you when he picked up on your vibe that you liked him a lot. But he acted like an asshole anyway by being all wishy washy and sending the mixed signals. Some people just get off on attention from the opposite sex. He probably just enjoyed your romanric interest in him. The threeway backstory says a lot about his attitude as well. You’re not crazy. It’s good you took some initiative to find out where he stands. Saved you some time.

    Hot debate. What do you think? Thumb up 4 Thumb down 6


    • michelle Says:

      THIS===>>>”He just didn’t want to be an asshole, sleeping with you when he picked up on your vibe that you liked him a lot. But he acted like an asshole anyway by being all wishy washy and sending the mixed signals.”

      He liked playing boyfriend but wasn’t going to take the charade further because then he’d be an asshole. I’m sure he thinks he was doing her a favor by not letting her pay for things and taking her out for her birthday.

      Hot debate. What do you think? Thumb up 5 Thumb down 5


  4. Parenting Says:

    The only thing that makes this crazy is the fact that its a man doing this to a woman and not a woman doing this to a man.

    Getting involved with both ex girlfriends following a threesome and trying to friend both of them sounds more like the behavior of a college boy than a 40 year old man. The same goes for his need to flaunt this soap opera to complete strangers.

    Maybe he strung you along because he was lonely and seeking female attention as Bree said.

    Like or Dislike: Thumb up 7 Thumb down 0


    • ATWYSingle Says:

      Like I said in the linked post, I don’t think this guy is a bad person. I think he’s a bad dater He was blurring the lines with his behavior, and I knew if I stuck around I’d get more invested in the attention.

      He never once stated explicitly that he just wanted to be friends until that text yesterday. I was under the impression that “let’s not rush through that door” meant he wanted to take it slow. Which, of course, is usually the universal battle cry for a time waster, but I liked him and decided to give him the benefit of the doubt. His actions supported my original interpretation, so I went with it.

      Where I side-eye him is the stuff with his ex-girlfriends. That three-way situation is insane, and only a crazy person would entertain it. I think he’s one of those guys who conflates confident and strong with crazy and insecure. His still very much tied to his ex, another point that made me wary of getting too close. I saw this guy using me as a placeholder while he got his shit together and then blowing me off when he got a girlfriend. That would crush me. I had to get out before that happened.

      Hot debate. What do you think? Thumb up 8 Thumb down 5


      • fuzzilla Says:

        **I saw this guy using me as a placeholder while he got his shit together and then blowing me off when he got a girlfriend. That would crush me. I had to get out before that happened.**

        Good for you. I have a friend who falls into that exact pattern a lot. Her other friends will be like, “Just have fun, see how it goes,” while I’m like, “GURL, NO. Don’t put all your eggs in this basket. Let his behavior be your guide, not just your feelings.”

        Like or Dislike: Thumb up 5 Thumb down 0


      • KK Says:

        I think he seems like kind of a shitty person. Maybe not a bad person, per se, but not a decent person at all. He was deliberately leading you on – you DO NOT wipe crumbs off a friend’s face. I also dont think he was using you as a placeholder, as that would mean he would be dating someone until the one he really wanted came along. He absolutely WOULD use you for emotional intimacy until a gf arrives

        Hot debate. What do you think? Thumb up 7 Thumb down 4


        • ATWYSingle Says:

          He absolutely WOULD use you for emotional intimacy until a gf arrives

          Yeah, I agree with this and think this is what was going on. The guy just doesn’t know how to be single and needs that companionship. What hurts is knowing he probably wasn’t attracted to me and did all this stuff anyway.

          Like or Dislike: Thumb up 5 Thumb down 1


          • Daryll Says:

            Men don’t usually invest the kind of effort (or money) you described on women they don’t find attractive. He’s probably sleeping someone else and doesn’t want you to know because he likes hanging out with you.

            Like or Dislike: Thumb up 2 Thumb down 1


          • Speed Says:

            “What hurts is knowing he probably wasn’t attracted to me and did all this stuff anyway.”–Moxie

            I don’t agree here.For the simple reason that, as another commenter above wrote, “the vast majority of straight guys are not out looking for female friends.”

            Degrees of attraction can vary, but I don’t think many guys are looking to get into game-playing stuff with women they have no interest in. I don’t think this dude is an exception.

            Like or Dislike: Thumb up 2 Thumb down 0


  5. Speed Says:

    “I think he seems like kind of a shitty person. Maybe not a bad person, per se, but not a decent person at all. ” KK

    I fully agree with this. I don’t think he’s some Machiavellian character planning to exploit and destroy women. However, he doesn’t seem to have any sense of boundaries or conventions, or “decency (which might be defined as adherence to social conventions)” as KK put it: he’s seem to be mainly an intellectual hedonist or a “follow your pleasure” type of person. These types of people seem to be very well-represented in online dating sites.

    But Moxie’s link to her Woman on Top blogpost was filled with unwarranted self-flagellation. Moxie gave this guy a shot, to see what he was all about. She got some good companionship, conversation and hints at romance. When he was evasive for a long period, she clarified things with a blunt “in or out” question. So, this guy was out. Perhaps she should have bailed earlier, or not gone out with the guy at all. But, as far as I can, she didn’t take some incredibly wild gamble with her heart. Had a few things gone differently (ex: this guy gotten a sudden jolt of maturity and clarity), Moxie could’ve gotten a big payoff. You can’t know what’s beneath the waves through sheer analysis. You have to dive in, and Moxie did. What’s wrong with that?

    The idea of someone, anyone being a “polished, perfect dater” is a fantasy that is heavily promoted online, but not even the most elite quarterbacks connect on every pass. This pass didn’t connect, but it takes nothing away from the QB.

    Hot debate. What do you think? Thumb up 8 Thumb down 2


    • mxf Says:

      I agree with you, Speed. There was enough initial interest for her to stick around and explore the situation, even if that in itself was uncomfortable, and when she reached her tolerance threshold for ambiguity, she sought answers and got them. Of course it’s disappointing that the outcome wasn’t a lot of fun, but I don’t get the feeling that Moxie misread the situation at all, or that there was a concrete answer that this guy was purposefully hiding from her all along. If anything, he doesn’t sound like he had any concrete answers until asked directly to flop one way or the other.

      I’ve gone out with people where I was interested enough to keep seeing them, without being wildly sure I definitely wanted to keep seeing them. Eventually I stopped doing that, but it was because I became more relationship-minded and less dating-minded. But back then, a direct question about my intentions would have made me bail, and rightly so, because I was drifting along without much purpose and that only works if both people are drifting the same way.

      Like or Dislike: Thumb up 4 Thumb down 0


  6. Robyn Says:

    I got tired just reading about all the complications and effort it took to even communicate with this guy / figure out what the heck he was talking about!
    If it’s that complicated…. that’s a sign that it’s not going to be a good match (be it for personality or timing/circumstance reasons or both).

    Well-loved. Like or Dislike: Thumb up 18 Thumb down 0


  7. Yvonne Says:

    I agree with Speed that this man has very loose boundaries and is a hedonist. The whole girlfriend, ex-girlfriend, met during a three-way was so confusing to me I had to read it 3 times. This man gets a big ego boost from drama. At this point in my life, that alone is off-putting to me.

    You were right the first time when you figured this guy wasn’t romantically interested. How do I know? He didn’t ask you out again. When a man is interested, he acts. He doesn’t sit there trying to read the tea leaves the way we women often do. He asks you out, period. He might even tell you that he finds you attractive and that he likes you.

    I do think he would have been okay with casual sex (hedonist/egotist again). That’s the tricky part in this scenario. He put some feelers out there, since he knew that you were attracted to him, like wiping the chocolate off your mouth, etc. I’d also hazard a guess that the sex potential was why he picked up the tab. If you would have initiated something physical, he probably would have accepted, but he wasn’t interested enough to initiate on his own.

    Like or Dislike: Thumb up 8 Thumb down 1


  8. Speed Says:

    The fact that this guy agreed to let you write about him, and is probably voraciously reading all this right probably also indicates he is a typical attention addict. Better off dating a coke addict than an attention addict. Coke addicts are more normal.

    Hot debate. What do you think? Thumb up 8 Thumb down 2


    • ATWYSingle Says:

      Okay, I know I keep saying this but: he’s not that guy. I’ve been involved with that guy, the guy who obsessively checks my site for mentions of himself, the guy who used me for attention and an ego stroke, the guy who thinks he’s a much better man than he is.

      I know that guy. Michael is not that guy. I wish he were, because then I could hate him and be angry instead of being sad and hurt. I would take anger over pain any day.

      He wasn’t after sex. If he was looking for that he could have gotten it. I don’t know where you people are getting this idea that he was investing this kind of time and money into getting something he could have easily have gotten without all that. That’s not how men work. If he wanted sex, all he had to do was make a move. He didn’t. Ergo, he didn’t want sex.

      I don’t think any of this was malicious. I think he just wasn’t attracted to me but liked my company. I just wish he had been explicit about his lack of interest from the start. That’s where he was selfish and wrong.

      Hot debate. What do you think? Thumb up 7 Thumb down 10


      • michelle Says:

        Michael might not be the Gareth version of that guy but he’s still that guy. Until you asked him point blank whether or not things between you two would become physical he skirted the subject whenever possible. At best he wasn’t direct about what he wanted because he liked spending time with you. At worst he knew how you felt and was using it to his advantage regardless of how that might affect you.

        “I think he just wasn’t attracted to me but liked my company.”

        Of course he was attracted to you. He wouldn’t have done all the things he did if he didn’t see the possibility of sleeping with you at some point. He was keeping you on the hook until he had a better idea of what he wanted. Some of us are privy to more intimate details of this story, like the stuff about his relationship with his ex-girlfriends, so I’ll just say I don’t think either of them are totally out of the picture and leave it at that.

        Like or Dislike: Thumb up 8 Thumb down 0


  9. Laura Says:

    I believe such guys know exactly what they’re doing. He knew how she felt and that she was going to stick around. He also knew wasn’t after anything substantial with her, but he enjoyed her company and the attention he was getting from her, so he kept at it for as long as he possibly could without looking like the bad guy deliberately leading her on. I bet he feels really good about himself for “doing the right thing” and being “honest” with her, while this situation would have never occurred in the first place had he really been honest from the start.

    None of this makes him a horrible person or anything, but it’s really not the epitome of fairness either. And I don’t think he meant to be hurtful or malicious, but those people simply care about themselves (and just as importantly, their self-image) much more than they do about the other person.

    In situations like this, I really wish people would either be VERY clear right from the start about what they can offer or simply disengage when they feel the other side expects something different or more than they can give.

    Like or Dislike: Thumb up 8 Thumb down 0


  10. Nia Says:

    I’m glad Speed is back in the comments, he (xie?) always seems to have a very crisp, clear view of things and a well spelled out point. I agree that this guy struggles with boundaries (and I had said that before, too) and is floating along, not sure of what he wants or is up for. I think there’s a chance he was hoping attraction would build or spark, or that perhaps he could coast on “enough” liking as friends to find that spark. I know occasionally friends do spark at first and then let it die, only to find the spark again. So it’s a possibility that he was hoping for this. I think that perhaps he also felt “it’s so close! Maybe one more date/hang out will put the pieces together”.
    I’ve been that other person, where the date has a lot of what I want and am looking for, but just lacks that last puzzle piece and it’s not clicking.
    For the record, I think he needs to
    Get 100% clear on his desires and attractions, and deal breakers/needs/goals
    Learn how to communicate nicely but clearly and directly “Thanks but no thanks”
    Learn how to separate friends from lovers or dates
    Learn how to meet women NOT through his friggin’ ex.
    Learn how to disengage politely and in a timely fashion

    So yeah, dudes got some workin’ to do.

    Like or Dislike: Thumb up 7 Thumb down 2


  11. BTownGirl Says:

    You’re giving yourself way too hard of a time here! It’s not like you wasted years on this and the only way to know what someone is about is to give it a shot. That’s not to minimize that it sucks because we’ve certainly all been there, but let’s not give this guy more importance than he deserves. It absolutely makes sense to be like, “You know what? I should have caught x/y/z and I’m really going to take a look at my process”, but don’t say you’re an idiot, because it’s just not true. Frankly, who gives a shit what his deal was, because the whole thing makes no sense. I think the best response to this is, “Next!” Do something nice for yourself and I bet you’ll feel much better in a few days.

    Hot debate. What do you think? Thumb up 9 Thumb down 2


  12. AnnieNonymous Says:

    I wouldn’t beat yourself up about this. Michael would cycle between being distant and then having dinner with you. This understandably gave you the impression that he was coming back to you and opening himself up for a relationship. You see now that he has a pattern of keeping women within arm’s reach and giving them false hope. The exes haven’t moved on. They still think they might get back with him.

    There’s a certain type of woman that men feel comfortable stringing along and keeping as a port in a storm. Be glad he doesn’t see you in that role.

    Like or Dislike: Thumb up 5 Thumb down 1


    • ? Says:

      yeah. Posters here were saying no normal straight guy would spare time and money on a woman he felt nothing for. But this is not a normal guy. He sounds narcisstic, if I may say so. He seems he get off on the attention and validation these women give him, and if sex is involved then all the better. I can’t imagine a guy having his two exes in the same dating profile picture as him, telling dates about his emotional and physical three way with an ex and her friend, and being happy to be written about in a dating blog. This doesn’t sound like normal straight guy behaviour to me. Not just perhaps narcissitc, but a touch exhibitionist as well

      Well-loved. Like or Dislike: Thumb up 10 Thumb down 0


  13. Matt Says:

    As usual men around here are damned if they do and damned if they don’t.

    Maybe he wasn’t ready to take the relationship further and that’s why he balked at Moxie’s aggressive ultimatum? Why does it have to be that he we stringing her along or using her for attention? If Michael were Michelle would you still be saying the same thing?

    Like or Dislike: Thumb up 3 Thumb down 3


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