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Dating a Friend’s Ex: Is it Ever a Good Idea?

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He’s cute. He’s nice. His glasses make him just the right amount of adorkable. And he’s newly single. What’s not to love? Oh yeah—he and your friend just broke up.

It wasn’t a totally bad breakup, but it definitely happened. However, you think there could really be something there between the two of you. What should you do?

Being interested in a friend’s ex involves treading in some pretty murky water, but that doesn’t mean it can’t be done. The double success of starting a potential relationship and keeping your current friendship depends on a few conditions. Consider the following questions to decide if it’s okay to proceed with caution or if it’s better just to let this crush go.

What was the nature of their breakup?

Did he break up with her? Did she break up with him? Were there tears involved? Wait, was he that guy whose teddy bear and mix CD she threw out the window?

Sadie, a junior at Missouri State University, knew her friend had broken up with her boyfriend, so she felt like it wouldn’t be the worst thing in the world if she tried to make something happen with him. “Of course, I talked to my friend about her breakup first to get the details,” she says. “I didn’t mention that was [why] I asking because I was interested in him until after she told me all about it. But because she seemed to be over the whole thing, I started talking to him.”

Sadie passed the first hurdle: Her friend was over him. But, be warned—while she may be over him because she did the breaking up, he may not be. If the breakup was mutual, your chances of success are much higher. No one wants to deal with lingering feelings.

Dr. Patrick Wanis, an expert in human behavior and relationships, agrees that it’s important to find out how their relationship ended before proceeding with your own. “For example, would you still want to date this guy [if] your friend reveals to you, ‘The reason we broke up is because he cheated on me’?” he says. “And you may not have known that before… It’s better to know these things in advance than find out later.”

How long did they date?

When deciding whether or not your friend’s ex-boyfriend could become your next boyfriend, take the length of their relationship into consideration. If they were high school sweethearts and continued dating into college, dated for four years and finally broke up because they didn’t see themselves getting married (because marriage was on the table?!), that is a complete different set of circumstances than if they had only dated for a few months in college.

Saint Louis University sophomore Lena and her ex-boyfriend dated for about seven months. When her friend came to her to tell her she was interested in her ex, she gave her the go-ahead. “We dated for under a year, so it wasn’t that big of a deal,” she says. “I feel like a year is a good cutoff time to determine if you should really be with your friend’s ex.”

Lena’s friend knew that Lena and her boyfriend had only dating for seven months, which, while respectable, meant that neither one of them was ready to propose any time soon. She felt like it was okay to seek Lena’s permission after realizing that seven months was nothing in the grand scheme of things.

Dr. Wanis says that in addition to figuring out how long your friend and her ex were together, you should find out if your friend’s ex is “emotionally free” of her. “There is no black or white answer of how long do I wait before I start dating again,” he says. “We have a belief, and this is a false belief, that time heals and that time heals everything. And it doesn’t. Time doesn’t do anything of itself. It’s an abstract situation. It’s what we do in that time.”

Have they both seen other people since?

After the breakup, your friend made it clear that she was over her ex. She made it so clear by subsequently finding another boyfriend and living happily ever after. It’s sickeningly cute, but you’re totally happy for her. Now you’re thinking it’s your chance for happiness, too. And, just your luck, the ex has already moved on as well. You wouldn’t be the first girl he’s been with since breaking up with your friend. The stars have aligned!

Rachel, a junior at the University of Mississippi, found herself in this ideal situation. “My friend and her ex broke up, but it was totally mutual,” she says. “What made it even better was that they had both already moved on to other people and didn’t seem to have any leftover feelings from their relationship. So, I went for it. I started talking to my friend’s ex.”

The mutual breakup paired with moving on to other people made this the perfect situation for Rachel. She didn’t have to worry about hurting anyone’s feelings, because both parties made it clear that there were none left to be hurt. When that’s the case, proceed.

Were you and the ex friends first?

You and he met freshman year, long before he started dating your friend. When he and your friend started dating, you were totally supportive. He was a great guy, after all. So, even though he and your friend broke up, that doesn’t change the fact that you know him well. And you know that he’d potentially be worth any trouble.

Emily, a senior at Loyola University Chicago, met Brendan freshman year. He lived on her floor and they became close, but she only ever saw them as friends. So, she hooked Brendan up with her best friend, thinking the two of them would be a good match. Her two friends dated for about a year, and during that time, Emily developed a crush on Brendan.

“When they eventually broke up, I hoped that he maybe felt the same way about me as I did about him,” Emily says. “And he did. He told me that I’d been in the back of his mind since freshman year.” They’ve since been dating for more than two years.

Even though Emily didn’t wait long after her friends broke up to profess her feelings to Brendan, she trusted that it would be worth it. She was close enough with him know (or at least hope) how he would respond. And she didn’t feel like she was choosing a guy over her friendship, because he was her friend, too.

Do you think being with your friend’s ex could ruin your friendship?

If you think your friendship could not survive the potential emotional trauma of dating your friend’s ex, you’re faced with a tough choice.

“I picked the guy,” says Rebecca, a junior at the University of Missouri – Columbia. “And I lost some friends in the process. I’m still figuring out if it was worth it or not. I ended up with the guy, but now I’m not friends with a lot of my friends because of it. They sided with his ex-girlfriend and my ex-friend.”

You’ll have to ask yourself if your friendship is worth saving. Is she someone on the outskirts of your friend group, or is she one of your best friends? Is he someone you could seriously see yourself with for a decent amount of time, or is he just a fleeting crush? The answers to these questions should help you determine if it would be better to walk away with your friendship or relationship.

Dr. Wanis advises collegiettes to have a serious conversation with your friend’s ex. Ask yourselves, “Are we truly committed to each other? Is this something we believe is truly long term?” And if/when you get a clear answer that it would be a long-term relationship and you would be committed to each other, you have to decide whether or not you would be willing to lose your friendship.

How does your friend react to your feelings?

No matter what you decide to do in terms of pursuing or even talking to your friend’s ex, it’s important to be honest with your friend about your feelings for her ex. If you’re serious about your crush on her ex, you should tell her. “I started talking to him, thinking that it would be okay because they had both moved on,” Rachel says. “Had I talked to her about it sooner, I think things would have worked out better for our friendship.”

Dr. Wanis says that it’s best to be honest when it comes to talking to your friend about potentially dating her ex-boyfriend. He even came up with a bit of a script to guide you in that conversation: “Jill, I know you’ve finished your relationship with John. Recently, John and I have been hanging out, and I haven’t told you about this. It’s just that we just started hanging out and feeling developed, and I would like to date him. And I am going to date him. And I don’t know how you feel about this. Obviously, I prefer you to be okay with this, but how do you feel about this?”

If your friend doesn’t take the news well, be sympathetic and understanding. Ask her to explain her feelings, Dr. Wanis says. He suggests you say something like, “Because, you know, now that you’ve broken up with him, someone’s going to date him, whether it’s me or someone else,” and then let you friend talk about her feelings toward the situation.

It’s important to note that there are always exceptions to the rule, as our good friends in He’s Just Not That Into You teach us. You could find yourself getting the best of both worlds: finding the love of your life and keeping your friend by your side. Who knows! But when it comes to boys and friends, tread lightly. Weigh your options. Be honest about your feelings. And then, make a choice: Proceed with caution, or walk away.


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