Should I sleep with my ex-girlfriend's best friend?

Dear Amie: I’ve recently broken up with my girlfriend of 5 years. It was a pretty messy break up but we’ve said we’re going to try and remain friends. Is it okay to try it on with her best friend now that we’re not together any more?

*crickets* … Are you insane, man? Let’s have a little recap on your question. “Recently broken up” plus “sleep with her best friend” does not equal “remain friends” unfortunately.

It’s 2019, you should be able to bang whoever you want right? You’re a free and single man now. You don’t have to answer to anyone, right? Well, sort of right, up until the part where you included your ex’s best friend into the equation.

They say the best way to get over someone is to get under someone else. I don’t know who said that but they forgot the fine print about that doesn’t include shagging your ex’s best friend in the wake of a messy break up. Literally the last thing you need after a messy break up is to turn it into a messy shit-storm for the sake of a root.

Ask yourself, how do you feel about your ex? Are you totally over her? The fact that you’ve said you both want to try and remain friends down the track, makes me think that being led dick first directly into a tricky territory will only obliterate any chances of a future friendship. If you respect your ex, it’s worth reconsidering. Although it might not seem a big deal for you, it might be for her. Maybe it’s not a big deal for her? Maybe she’s an anomaly and she might be happy for you. However, if you have to ask, you probably already know how she’s going to feel about you going to town on her BFF. Respect what the two of you had and avoid having any sexual relations with people who are in your ex’s friend circle. It will only end in tears.

Maybe the ex did the dirty on you and her bad behaviour is why you’ve broken up? Maybe she had sex with your best friend behind your back while you were together? Are you wanting to sleep with her bestie to be vengeful? Maybe you’re thinking that’s justification and fair game for sleeping with her friend? Maybe, but if you value the friendship, and, you’ve already said you’re both working towards a friendship, be the bigger man and don’t add drama to your life for the sake of an orgasm or three.

With that being said, maybe it’s not just a sex thing. If you feel like you could have genuine feelings for the friend, or that she might be the goddamn love of your life, of course you should go for it and just deal with the fall out of potentially losing the ex… Life’s too short and all that, but I’d recommend letting the dust settle a bit first. Your move, my friend!

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  • prettyg123 Photo
    More than a month ago

    Big no no. Why have all these headaches when there are plenty of fish? Don’t dig a hole for yourself.

  • krow16 Photo
    More than a month ago

    Isn't life too short for this 'boyfriend-girlfriend' bullshit??

    If the breakup was messy, do both yourselves a favour and FORGET ABOUT BEING FRIENDS. Unless you're both desperate for friends.

    Test the waters with her friend if you think there's genuinely something there, and if it's not, well, move on. Neither girl needs you as a friend, and I'm sure you probably don't need either of them.

    Why even bother asking for advice. Just do what you want according to how you feel and accept whatever comes next. Good or bad. But don't be a douche and try to backtrack if it turns out to be a mistake. Own it and move on.

    1,2 or all 3 of you could be dead next week...and this conversation won't even matter.

  • allinmymind
    More than a month ago

    Sorry this is a bit like Days of Our Lives.

    • mandgee
      More than a month ago

      Days of our wives?

  • Bigdawg71
    More than a month ago

    If you want more drama than a millennial Drag queen convention spiked with Valium and alcohol mourning the death of Joan Rivers, go for it. Or why not bang her sister in the process as well.
    Other wise snap out of it you dick.

  • Auscoco67 Photo
    More than a month ago

    A definite no-way!

  • TopShelf.
    More than a month ago

    Absolutely not!

  • 321cba Photo
    More than a month ago

    Obviously they're not that best of friends if she's going to take him on

  • Gwendolina03
    More than a month ago

    no way are going to find me sleeping with my ex boyfriend’s best friend. Holy cow you’d think there was a shortage of cocks and pussies definately ain’t going there. Good luck!

  • funguyatbyron Photo
    More than a month ago

    why not if she wants you go for it if the ex wants one of your mates it's all ok you may end up in a hot steamy foursome you only live once

    • MaleOnQuest Photo
      More than a month ago


      boyfriend + ex-girlfriend + Ex-girlfriend's BFF = threesome

    • barkly48 Photo
      More than a month ago

      MaleOnQuest.... the way I read it... boyfriend + BFF... Ex with boyfriend's mate, equals foursome....

  • looking70s
    More than a month ago

    No way in hell, you said you you would remain friends, what would that do to your ex?, but it you try stand by for her friend to reject you and make you the laughing stock.

  • KinkyGirl101
    More than a month ago

    Hell. No.

    More than a month ago

    Bit disrespectful, you won’t be friends after she finds out, and they always find out, also who says her friend even wants you ? You sound selfish there’s heaps of other woman you can be with why go for her bestie unless you are just wanting to make trouble for yourself. Total dick move you x dodged bullet if you’ve been thinking about her friend all these years.

  • MissThatTouch
    More than a month ago

    Apart from the fact he wants to 'try it on' (what a charmer...!) which usually implies you have no idea but will try anyway - I don't think he has any idea how loyal, female best friends are or can be, to each other lol. Amie Wee's (author) response is absolutely spot-on, with the messy shitstorm this want to 'try it on' with her, is very likely to create....he better be prepared for that, from both angles (the ex, and the best friend - especially if the best friend has never shown any signs of attraction towards him).
    Does he really want to create this for himself (and them) for the sake of getting laid?
    (Of course, we don't know the full situation, and attraction between best friend vs him may have already come to play (although, again "try it on" implies this isn't the case)...but, I'm just going by what we've been told here).

  • AmyF2016 Photo
    More than a month ago

    Sounds like a typical male...think with your dick and assume everyone wants to have sex with you

    • Account Closed
      More than a month ago

      Better than thinking no one wants to h as very sex with you ??

    • Account Closed
      More than a month ago

      Welcome to the male race Amy.

      Guy are biologically programmed to have sex. Monogamy is simply not in our nature and don't be fooled by feminism telling you otherwise.
      Its just an 'IS'.

      The article could have used slightly different wording - guy has always fancied his girls BF forever, and he's free to explore that......the question is, should he?

    • IceCubeDouble
      More than a month ago

      Let's see how this scenario works logically:

      1. Messy breakup and remain friends .....something doesn't make sense.

      2. He is free - she is free - what seems to be the problem?

      Answer - typical jealous mentality "You shall not have what I once had". Move on from this Victorian era way of thinking.

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