I seem to have got myself into a little dilemma – really appreciate anyones thoughts.

Split up with ex of 18 months in November. I’ve struggled, really badly, agonised over it.

But did try dating in Feb – met a lovely lady but we both freaked out about our exes and realised we couldn’t do it. But we stayed as friends, it’s been lovely, the healthiest thing I think I’ve ever done. Talked about exes, dating (she then dated a few people). Fwb where the benefits are just I care about her, help fix things about her house, we go out to dinner and she helps me deal with me agonising over ex. No sex after the first attempt.
So all the while it’s let me heal. I didn’t date anyone but a few weeks ago gave it another try.

I met a lovely lady. Instant chemistry and attraction.
But in that week me and friend had got a little tiny bit flirty.
She was then annoyed when I told her I had a date – and it was looking promising. (Remember she’s had a few)

And I’ve just had a messy weekend where they both knew I was seeing both of them. And on each date we slept together. I’ve never done this and feel somewhat ashamed. And they both know and are fairly chill about it.

Anyway. Friend now wants to date exclusively but casually(!?) – understanding I didn’t really want to rush into a big relationship (all I’ve ever done)

The lady I dated would have been fine with me dating both, with sensible boundaries. But I don’t think I can do it.

Anyway. Wtf is wrong with me. Most guys would be having a wild time – me I just don’t want to hurt anyone and full of anxiety and worry 🙁

(I’m 42)

16 comments
  1. People are built differently. If you don’t want to date both, that’s perfectly OK and normal. Some people like to play the field a lot, others are more comfortable seeing how one thing works out. As long as you’re not hurting anybody, do what you are happy with.

  2. What’s good for the goose was NOT good for the gander in this instance. She didn’t want you, but she certainly didn’t want anyone else to have you either.

    To me this reads as if the original woman got jealous when she found out you had another option. If you break it off with a new woman and decide to date the original woman exclusively, it won’t be long before the original woman decide she wasn’t ready after all. By then the new woman will be gone. Cut the first one loose. Quit giving her boyfriend benefits.

  3. Kudos to you for expressing this mate. Most guys would probably give you a hard time. I’ve been there and it’s not great. Do what your head and heart says and above all, make yourself happy.

  4. Met girl post breakup of a 3+ year serious relationship. I was too heartbroken to jump into new relationship. We hooked up and were fwb for a little bit, transitioned no problem into friends. Kept in touch but weren’t super close. Fast forward to start of covid we start talking and are both single. We were both feeling lonely with the restrictions so decided we would bring each other into our “bubble” and hang out. Eventually we slept together and for some stupid reason I pushed the just friends narrative. Biggest regret of my life.

    Eventually it fizzes out again and she meets someone. They are now engaged. I’m happy for her, but giant regret of mine.

    The regret sucks. I wonder if she was the one and I’ll never get that answer.

    Sit down and communicate with her. If you want to be in a relationship with her, tell her. But my advise is to not leave it as a what could of been. Don’t let it be a situation where you both had feelings for each other but just sucked at communicating it. That being other comments have said it could be her just being jealous. Feel it out, but communicate what you want.

    Side note – You’ve already been close friends who most likely have a deeper emotional connection. At this point rushing into a big relationship most likely should be don’t move in together next week, don’t share a bank account, don’t make a large purchase together. Stuff like not communicating or worry about when you see each other next is not normal relationship behaviour.

  5. >Fwb where the benefits are just I care about her, help fix things about her house, we go out to dinner and she helps me deal with me agonising over ex

    these are all benefits for her except the last one that takes no effort. you do all that and all she has to do is not talk while you complain about how sads you are about your ex.

    >I met a lovely lady. Instant chemistry and attraction. But in that week me and friend had got a little tiny bit flirty. She was then annoyed when I told her I had a date – and it was looking promising. (Remember she’s had a few)

    yeah she knows this woman won’t be ok with you doing all this stuff for her and she’ll lose a guy who does boyfriend shit without her having to do any girlfriend shit. she doesn’t want you. she just doesn’t want anyone else to take you away.

    >Anyway. Friend now wants to date exclusively but casually(!?)

    yeah. like i said.

    >The lady I dated would have been fine with me dating both, with sensible boundaries. But I don’t think I can do it.

    do it.

  6. What if you took sex out of the equation and continued to see both? With both being aware that you are not exclusive with either of them? I don’t think it would hurt to do that for a bit. I think your original lady is jealous. Or she may be realizing feelings that she didn’t acknowledge before. But you know her better than internet strangers.

  7. I think you’re purposely sabotaging yourself. Nothing happened with your “friend” until you met someone new. Then and only then, the relationship turned sexual. Prior to that, not crossing that line kept her at bay a bit. There was emotional intimacy but not physical. Now that someone else is in the picture to keep you from getting too close, you could allow the physical intimacy. And she’s likely mirroring you with the same behavior.

    Typically dating more than one person at once for an extended period is a tactic to not get too close to anyone. That makes sense intially when you want to pace things and not overly invest too soon, but you’ve already passed a line with the first woman by becoming close emotionally. Can’t go back in time, and this probably won’t change your desire to not be exclusive with anyone.

    But they told you want they want and now you have to decide, even if that’s not what you exactly want. The “friend” isn’t giving you the option to see both. If you don’t want exclusivity, the other is open to that for now, likely because there’s not nearly as much emotional investment yet. So you handle it by being honest and turning down the friend since it’s not what you want, and you distance yourself from her or else you’re leading her on. Then you’re honest with the new woman that you don’t want exclusivity.

  8. I think if you really really wanted to be with your friend at this point, you’d know it. I think what’s really happening is that you’re afraid of being left with no options or only being left with the option you realise you don’t want. That in itself shows you what it is that you actually want right now – options. So, I say follow that path, honour that need, with no regrets.

    Personally, I’d tell both of them that I’m not willing to be exclusive with anyone in general for the first few months. You need more information to go on, and you can’t get that information without exploring things. It’s not even about choosing between them. It’s about doing what feels right to you in any given moment.

    The other option is that you date your friend and see what happens, hopefully leave it on good terms with the other woman, and maybe you will explore that later down the line if the stars align.

    Of course, the third option is that you consider solo polyamory. 🙂

  9. When it rains it pours, eh??

    I have no advice for you, other than trust your gut. Good.luck.

  10. Tell them both you love the other person more, and go with the one that truely wants to see you happy. Not just have you as a trophy.

  11. advice for when one is lost is to stop.

    idk if youre totally lost, but try to prioritize the self who inhabits you more deeply than the self who reacts to the worries. youre full of them, and youre subject to lose yourself, dont let them inhabit your mind, journal, and have a glimpse at the notion of unconscious shame in yourself without needing to express it to them. there’s no yes without no.

    this is all easier written and visioned than embodied, but the situation is rich and you may potentially find a way, if you can keep being honest without needing to be forthright, for it to create a new, stronger force in you that is more able to adhere to the deeper self that doesnt need from either one of them.

    and if you compare yourself or the situation to what other men think or say again, you can now know youre fooling yourself with your judgements, so stop the idiocy. your heart is clearly on the way towards deeper purity and sending you initiative to begin to have more control over the manifestations that come from dangling little you. how you deal with this and what consequences arise is less your concern than experiencing what nature is communicating to you inside yourself through the situation it’s granted you.

    think about it, too, dispassionately. stop the malarky through sincerity. youll have to write, otherwise your reactivity will get too intense for you to control it.

    think about this too: what meaning and implication about relationships and your understanding of women is hiding under the surface of this situation? you need to examine yourself deeply, without them, and start willing, not easy, we’re all full of unconsciousness.

    if you keep judging yourself youll just isolate yourself, so instead of doing that unconsciously take a stop in yourself without reference to either of the very nice women you describe.

  12. Ah the everlasting curse of a fwb situation. Though they maybe convienient, I often warn that it puts blinders on you. You end up missing good opportunities because you’re busy fucking around (literally) with your fwb.

    You might have a possibility of a future forever partner. But right now you might settle for a familiar exclusive but casual relationship?? What even is that?

    >Friend now wants to date exclusively but casually(!?)

    Yeah, that doesn’t make any sense to anyone either.

  13. Yikes…i got a bit lost there… is it possible she got jealous of losing you as a friend? Or not having that bond with you? Or is it that she truly caught feelings for you. Freaking feelings…I swear if I could sell mine on Etsy I would…not worth the trouble.

    Might I add I think it’s great that you are thinking about not wanting to hurt anyone…Those feelings…

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