Sometimes in a relationship, you’re not sure how to phrase a delicate subject or tricky topic. Sure, saying nothing at all is easy, but avoiding the subject doesn’t do anyone any good. Awkward Conversations provides you with a template for what to say — and what not to say — and why, so you can have those difficult discussions without them turning into full-blown fights.
There are some unstated rules that we live by when it comes to dating. One of the most common? Your friend’s exes are off-limits. This makes total sense as you don’t want to sabotage your friendship.
But what if you suddenly develop feelings? And what if we told you there was a sensitive (and thoughtful) way to go about asking your friend’s former flame out?
Here’s a helpful guide for anybody who’s fallen for their friend’s ex-girlfriend. If you’re not sure how to go about it, we’ve got you covered.
No matter what the situation is, your friend should be the first point of contact. Even if you dread having this conversation, you can’t avoid it. Just think of how livid he’d be if he finds out from somebody else. Be gentle and honest while reassuring him. Also, be prepared for him to react to the news at first, be reassure him that it’s not a betrayal. It’s not like you actively sought out his ex.
Let him know that he’s your first priority, and that you’re never going to jeopardize your friendship by doing something he isn’t cool with. Show him that you respect his limits, and that friendship comes first.
Acknowledge that it’s not an ideal situation from the get-go. Yes, it might be awkward, but this is best practice. As she may be worried that her ex will be mad at both of you, put her mind at ease by saying there’s nothing covert going on. If you ask her out without mentioning your friend, she might think you’re going behind his back and being shady. That’s the last thing you want.
Chances are that when she started dating your friend, she put you in a platonic mental slot, too. That’s fair, as we often do that with our partner’s friends. When you decide to ask her out, have some romantic flair, but give her a moment to adjust to the idea of you transitioning from friend to potential boyfriend.
Be considerate. She can think about whether she doesn’t feel the same chemistry, or whether she’d like to go on a date with you.
Don’t pretend like the past doesn’t exist. Yes, she did date your friend, but that’s come and gone. Don’t bring it up over and over again, or badger her with questions about their past relationship going forward.
Instead, make it clear that you are going into this with no assumptions or biases about her. She’s much more likely to be receptive to the idea if you treat her like anyone else you met on a dating app or at the local bar.
One of the most graceful things you can do is show that you can handle rejection like a champ. She’ll be conflicted about what to do even if she likes you back, so don’t force it. Your best bet is to demonstrate to her that dating you will be worth it — you’re a grown-up, and you know it was a bold move asking her out in the first place.
Do what you need to do, but accept whatever the outcome may be.
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