I’ve started dating my best friend – but it’s all wrong

I’ve started dating my best friend – but it’s all wrong

dating former best friend post

I just started dating a guy who’s been my best friend for many years. I’ve known him for years, liked him right from the start and was obsessed with him until we started dating, but now it feels wrong. Firstly, it hasn’t even been a week but already he’s told me that he loves me. Secondly, he’s EXTREMELY clingy. He needs to be around me 24/7 and know everything which also gets on my nerves.

I haven’t said as much, because I don’t want to be rude, and because he’s always been my best friend – but this guy as a boyfriend isn’t everything I hoped. I’ve tried to give him subtle hints that I need my space and I’m not used to all this ‘togetherness’ but he doesn’t get it. And, while he’s pouring his heart and soul out to me, my subconcious mind is thinking about how to break up with him and preserve our friendship. I don’t even want him to kiss me. Friends are telling me that I’ve been obsessing too long and now I’ve lost interest and I’m a skank. Others are saying that I love him but I’m nervous that I might actually be happy with him. In any case, it is emotionally draining. I’m confused and don’t know what to do. Ashley

The whole friends-to-lovers thing can work, don’t get me wrong, but sometimes, I think male/female friendships remain platonic for a reason. You never get it on because you’re just never meant to, and although there may be the occasional ‘what-if’ frisson, it never quite catches the spark. We’ve got to acknowledge those not-quite-right feelings – especially if we’re lonely and single – and not force a thing that’s not really there in the first place.

I’m not saying NECESSARILY that this is what you’ve done, Ashley, but let me tell you a story. When I was in my early 20s, I became fixated on a male friend. He’d been my faux boyfriend for years, and I completely romanticised what it might be like if he were my, you know, real one. Then the planets aligned, and one afternoon we found ourselves making out at his house. Immediately, I wanted to stop. It was nothing like the fairytale fantasy I’d built up in my head, and I manufactured an excuse to leave because I couldn’t wait to get out of there and do a spider dance of wrongness to shake it off.

Your guy is a great friend, but that’s where it ends. For you, anyway. And that’s OK. It’s okay even if he’s madly in love with you. Sure, maybe you had a part to play in orchestrating the move from platonic friends to more – but that doesn’t mean you’re required to find a reason to stay together when you know you’re not feeling it. You can be sorry about that, you can love the guy to bits on a platonic level, but you don’t have to pretend or or try and convince yourself that all those sexy feelings are about to click in. You don’t even want the guy to kiss you and to me that’s a big red neon sign – with flashing lights – that says You Are So Not Into Him. Romantically that is.

So, treasure. My advice to you is to see this for what it is (a kinda strange lapse of judgement). End it now, before you or he gets any more knee-deep than you already are. Chances are, you’ll feel relieved, and while there are sure to be hurt feelings (and possibly imminent heartbreak on his part), if you’re kind about it, and straight up about it, maybe in time you guys can salvage the friendship side of things.

Love, reality chick

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Freelance journo, blogger, self-appointed advice-giver and co-author of Get Lucky. If you've got a dating or relationship issue, feel free to ask a question. (PS. You can also find me at The Mama Files and Letter To My Ex).


  1. Stephanie bretts 4 years ago

    I’m having this problem too, me and this guy have been best friends for a long time and we just recently expressed our feelings for each other. At first I felt like I was finally living a fairy tale, a guy I like actually likes me back! But then he wanted to start dating so I relentlessly said yes and we have been dating for a week or so. He is already saying”I love you” and planning our first date and it is all just so overwhelming. He has also said he wants to teach me dance which just makes me sick at the thought of it. Isn’t know how to break it off with him since he has already poured out his feelings to me and I just can’t say anything or else he will get to attached. His morning messages make me feel so regretful and I’m running out of excuses to not talk to him and I need some help

  2. real deep love 6 years ago

    it can also be great, it all depends on how both of you handle it. if the transition from friends to lovers went on naturally then it’s gona be cool

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