But what if you really, really fancy Sally, to the point you're picturing sleepy Sundays and all sorts of lovely, luscious romance? Is it worth pursuing? My rule of thumb is that it's fine unless it is a very good friend. If it's a close friend, proceed with caution.
6 questions you should ask if you want to date your ex's friend
Nana points to the story of her friend Katie, a year-old Londoner who lost a friendship when an ex got involved. If you're swept up in love and you simply must date the ex of a close friend, experts recommend you sit your friend down. Even if it hurts your pride, check with him that it's OK. LaCota stresses the conversation is worth having if you really think the girl might be your 'special someone'. During the conversation, pay attention to your friend's non-verbal communication.
Dating Your Friend's Ex - AskMen
At the end of the day, dating a friend's ex is going to be tricky territory all around. It's probably best if you can avoid it. If you can't, be prepared for potential complications and be realistic that you might lose a good buddy.
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And dwell on the fact that some of your excitement might just come from the taboo nature of this potential relationship, because, like everyone else, you want what's off-limits. If I were a betting man, I'd bet that your crush on this girl is just like any other crush.
Be prepared for consequences you might not like
It's a fun illusion, which, if pursued, might reveal a great relationship, or might not. Odds are, that's what this is, in which case you should probably just sigh, move on, and hit up your online dating site of choice, where you can find lots of other crush-worthy women. I found out about this the hard way, in a similar situation. Tom, one of my childhood friends, was always kind of bummed out, until he met Josie, a fast-talking, high-energy woman who brought him out of his shell. They had a sparkling relationship — they were one of those couples that just radiated warm, gooey, nauseating passion — and I was super envious of it.
Also, obviously, Josie was an outrageously foxy person: There was only one weird thing about her, which is that I would occasionally catch her looking at me a little funny. I suspected that she had a low-key crush on me. About a year after she dumped Tom abruptly, leaving him a sniveling wreck, I discovered that I was correct.
6 questions you should ask if you want to date your ex's friend
We ran into each other at a party. Flirting with each other was easy, taking each other's clothes off was easy, and it felt like fate — like absolute magic — and it kept feeling like absolute magic for about a month, at which point I discovered that she was kind of boring, or at least that we bored each other. In the end, I got about five dates out of it, in exchange for an irreparably ruined friendship. Tom found out, and he never forgave me. Now, if you're sure that this is not you, that this is Real Love you're looking at, then what you have to do is tell your friend what's up.
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Tell your friend about your intentions, and ask him if there's any way you can make the process easier for him. This conversation will not go well.
Because, again, you're declaring to an old friend that you're prepared to disregard his feelings. That's the truth of the situation. There's no two ways about it.
It's going to hurt even if you say all the nice things you should say — that you're still going to be his friend, that you're going to try not to Instagram this girl obsessively, etc. Ultimately, dating a friend's ex is inadvisable.
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There are pros and cons to all of these scenarios. Normally, there are only a two people you ever have to consider when you start dating someone new: Who cares about what other people think? This is usually solved by being up front with both your ex and their friend and asking. But friendships are complicated.
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