The Proper Way to Date a Friend’s Ex Without Causing a Problem
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.
1. Talk to Your Friend First
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.
“Hey, man. There’s something I’ve been wanting to talk to you about. I think Sophie’s really great, and I recently had thoughts of asking her out. I wanted to ask you how you felt about that because it’s been a while since you dated her. I would never do anything that hurt you, though. You’re way too important to me for that.”
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.
2. Be Transparent With His Ex
“Sophie, I don’t just think of you as a friend. I really want to take you on a date. I talked to John about it because I didn’t want to step on any toes. I know it might be weird for you, but I didn’t want to miss my chance to ask out somebody amazing because they dated my friend a few years ago. What do you think?”
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.
3. Let Her See You in a Different Context
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.
“You don’t have to answer this right away — in fact, why don’t you take some time and think about it? Text me whenever you want, no pressure.”
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.
4. Acknowledge the Past, But Don’t Dwell on It
“Sure, we already know each other, but that was in a very different context. I don’t want our opinions of each other to be swayed by that. I’d really like the chance to start fresh … what do you think?”
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.
5. Reassure Her That This Won’t Ruin the Dynamic
“Sophie, I just want you to know that your answer won’t affect how I feel about you. I know we are mature adults, and I respect both you and Nathan very much. Whether you’re interested or not, that’s not going to change what we have as friends.”
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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