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Woe Is Me! “I Cheated on My Boyfriend With a Friend. How Do I Not Lose Them Both?”

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Sep 12, 2021

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Image credit: Jeevan Mrityu (1970)

Woe Is Me! is a series in which The Swaddle team indulges your pity party with advice you’ll probably ignore.


I have a boyfriend of two years, but sometimes I think we’re better off as best friends. Yesterday, I got drunk and made out with a guy I kinda vibe with and I’m feeling guilty for cheating on my boyfriend. I don’t want to lose both of them. What should I do?

— The heart doesn’t lie

DR: Well, I guess you’re already aware that you’ve kinda messed up — but hey, it’s not too late to do right by them. First, I think it’s really important that you break up with your boyfriend. I think continuing to date him, despite thinking you’d be better off as friends, is unfair to him. I mean, he’d probably be better off with somebody who genuinely wants to be with him. Now whether or not you want to come clean about making out with a friend is up to you. However, word of warning: if you’re planning on dating the individual you made out with while continuing to be friends with your present boyfriend, they may inevitably cross paths, and the fact that you made out with one of them while being in a committed relationship with the other could come up, and potentially leave you at the same crossroads you’re at now — on the verge of losing both of them. So, do remember to think that through. 

SS: Hi, I don’t set much store by sexual fidelity-rooting thinking in relationships, but if you and your boyfriend have communicated to honor that, I can empathize with why this must be so nerve-wracking for you. This sounds like a pretty self-damaging action you’ve taken, and instead of jumping to “saving” your relationship or friendship, maybe you should take a look at what led you to act like this. It looks very unlikely that you would receive immediate forgiveness, and I don’t think you should be looking for one right now. I’d advise you to turn inward and fix what’s hurting in you. Get to know yourself a little better, be a better partner and friend to yourself, understand your ideals, and then look towards the people you hurt. Reparations cannot happen without introspection and healing. You deserve to be a better version of yourself. Take care.

PR: Please tell your boyfriend. COMMUNICATE. You can’t expect this to go well, regardless you have to let him know everything. How you feel you’re better off as friends (which basically means you’re going to have to cut him off to have sanity left in both your lives.) The fact that it became easy for you to make out with someone else based on a vibe check proves that you need to break it off and not lead the person on. And if for some reason you change your mind to continue wanting to date him, you need to let him know and hope that the trust is built back up, where you’re the one who is going to have to show some concerted effort (to say the least).

I am afraid but you can’t keep them both, that’s not how it works. There are only two ways for that possibility: One – somehow, both your boyfriend and this other dude are completely fine with this arrangement. Which I doubt is likely, which brings me to Two – Your boyfriend has a screwed-up way of being supportive of your choice and sticks around even if it hurts his guts. So, either way, you’re going to have to communicate everything to both the people, and don’t expect that you’ll get to keep them around. Know that you have screwed up not because you made out with someone. You have screwed up cause you failed to communicate what you felt about your relationship with your boyfriend and have broken his trust and not been honest. Best of luck to get out of this sticky situation…

RN: If you ask me, it’s best to just tell your boyfriend. The guilt will probably weigh on you and change your relationship; it may even compel you to come clean to your boyfriend later. The sooner you are honest with him, the less messy it might be. Your feelings aside, it just is the respectful thing to do to be truthful to someone you care about. There are also obviously cracks already if you feel he’s better off as a friend. So this might be the opportunity to be honest with not only him but more importantly, yourself, about what this relationship means to you. The other guy can perhaps come into the conversation later, it may be best to take things one at a time.

AS: Assuming you and your boyfriend were in an exclusive relationship, it looks like you messed up. I know, shit happens. But unfortunately, it happens and then there are consequences. You may lose your boyfriend over this because ultimately it’s their decision if they want to continue seeing you/being friends with you. As for your other friend, I think it might be best to come clean to them too — in case you haven’t already — because no matter what kind of relationship you see with them in the future, being dishonest will give it a bad foundation. I think in this situation all you can do is sincerely say your piece, but whether these people will still want to be friends with you is out of your hands. 

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Written By The Swaddle Team

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