This whole thing with dating your friend's ex is such a minefield. Everyone's got an opinion, but nobody really knows what the hell they're talking about. Some people act like it's the worst thing you could possibly do. Others are like "who cares, follow your heart!" But real life is messier than that.
I've been thinking about this a lot lately because I've seen it go both ways. Sometimes it works out great, sometimes it completely destroys friendships. The tricky part is figuring out which outcome you're headed for before it's too late.
Why Does This Feel So Taboo Anyway?
Okay, so why does dating your friend's ex feel so wrong even when technically nobody's doing anything bad?
I think it's because we're all kind of territorial, even when we don't want to be. Like, I still get annoyed when I see someone else at "my" table at the coffee shop I go to every morning. It's stupid, but that's how brains work.
Plus there's all this "girl code" and "bro code" stuff we grew up with. My older sister used to tell me that dating your friend's ex was basically the ultimate betrayal. But where did these rules even come from? And do they actually make sense?
I looked into it a bit (yes, I googled "why can't you date your friend's ex" at 1 AM), and apparently it's pretty normal in lots of places to date within your friend group. The whole taboo thing might just be something we made up.
But even if the rules are arbitrary, the feelings are real. When someone you care about starts dating your ex, it can bring up all sorts of weird emotions. Jealousy, sure, but also this feeling like you're being replaced or forgotten.
And then there's the group dynamics thing. Friend groups are fragile. When two people in the group start dating, it changes everything. What happens if they break up? Do people have to pick sides? What about group trips and parties?
I've seen entire friend groups fall apart because of this stuff. But I've also seen groups where everyone dates everyone and it's totally fine. So maybe it depends on the people involved.
Actually Think About What You're Risking
Before you do anything, you need to figure out what you're potentially losing here.
Are we talking about your best friend since middle school, or someone you met through mutual friends six months ago? Because losing a lifelong friendship over a crush is pretty different from making things awkward with an acquaintance.
I learned this lesson the hard way in college. I had this huge crush on my roommate's ex-boyfriend. They'd dated for like three months, broke up pretty amicably, and I figured it would be fine. What I didn't think about was that my roommate was also one of my closest friends, and things got weird fast.
She said she was cool with it, but I could tell she wasn't. She'd get quiet when he came over, and she started spending more time at other friends' places. Eventually she moved out. We're still friends now, but it took a while to get back to normal.
Your friend's personality matters too. Some people are naturally more chill about this stuff. My friend Chris actually tried to set up his ex with his buddy because he thought they'd be perfect together. But his sister would probably never speak to someone who dated her ex, even if they'd only gone on like three dates.
And think about your whole friend group. Are you potentially messing up everyone's dynamic? If you all hang out together constantly, dating someone's ex could create permanent weirdness that affects everybody.
The Details of Their Relationship Actually Matter
Here's something people don't think about enough - not all exes are created equal.
If your friend hooked up with someone a few times or went on a couple dates, that's very different from a serious relationship. I've seen people get super upset about someone dating a person their friend barely even knew, which seems pretty unreasonable to me.
But if we're talking about someone your friend was in love with, lived with, or talked about marrying? That's a completely different situation. Those relationships leave deeper marks, and your friend might have stronger feelings about you dating that person.
The breakup matters too. Was it mutual and friendly, or did someone get their heart broken? Did cheating happen? Was there drama or manipulation? These aren't just details - they're important factors that could affect how your friend reacts.
My friend Lisa dated this guy for two years, and he cheated on her with her coworker. When another friend started flirting with him months later, Lisa was devastated. Not because she wanted him back, but because it felt like nobody cared about how badly he'd hurt her.
Time is probably the biggest factor though. Dating someone's ex two weeks after they broke up is completely different from showing interest two years later. There's no magic timeline, but generally the more time that's passed, the less likely it is to cause problems.
Reading the Signs
After watching this play out more times than I can count, I've started to notice patterns in what works and what doesn't.
Good signs:
- The relationship was short or casual
- It's been several months since they broke up
- Your friend seems genuinely happy and has moved on
- Your friend group handles drama well
- Your friend has made comments suggesting they wouldn't care
Warning signs:
- The relationship was serious and involved real feelings
- Your friend says they're over it but acts jealous or weird
- The breakup was recent but everyone's pretending it's fine
- There's been other drama in your friend group lately
Don't even think about it:
- The relationship was serious and ended recently
- There was cheating, abuse, or other serious problems
- Your friend has directly told you not to pursue it
- You think you might be more interested in the drama than the person
That last one is important. Sometimes we develop crushes on people just because they're off-limits. It's that whole forbidden fruit thing, and it's way more common than people want to admit.
Be Real About Your Motivations
This is the uncomfortable part that nobody likes to think about, but you need to be honest with yourself about why you want this.
Would you be interested in this person if they weren't your friend's ex? Sometimes we get attracted to people just because they're forbidden. I knew someone who realized she was only interested in her friend's ex because she was mad at her friend about something else. Once she worked through that anger, the crush completely disappeared.
Are you looking for a real relationship, or are you just bored and want some excitement? Are you dealing with your own relationship drama and looking for a distraction?
Think about the future too. Can you actually see yourself with this person long-term, or is this likely to be a short-term thing? If it's probably going to fizzle out in a few months, it might not be worth potentially damaging a friendship.
Having the Conversation (If You Decide to Go There)
If you've thought it through and still want to pursue this, you absolutely have to talk to your friend first. This is not optional.
Don't do what my friend Mike did and just start dating someone's ex without saying anything. His friend found out through Snapchat, and they didn't speak for like two years. It was completely avoidable and really stupid.
Pick the right time and place. This isn't a conversation for when you're out with a group or when your friend is stressed about work or school. Find a private moment when you can actually talk.
I usually start with something like: "Hey, I need to talk to you about something kind of awkward, and I hope you know I care about our friendship too much to hide this." Then be direct: "I've been developing feelings for [name], and I wanted to talk to you about it before anything happens."
Don't expect them to have an answer right away. Your friend might need time to think about this. They might be totally fine with it, or they might be hurt and confused. Both reactions are completely understandable.
Pay attention to body language too. Sometimes people will say they're okay with something when they're really not. Look for signs of discomfort, and don't pressure them to give you their blessing.
If You Get the Green Light
So your friend said they're cool with it. Great! But don't think you're home free yet.
Keep checking in with your friend, especially at the beginning. Ask how they're feeling about everything. Be genuinely open to their feedback, even if it's not what you want to hear.
Be smart about social situations. Group hangouts might be awkward for a while, and that's totally normal. Don't be all over each other in front of your friend, but don't act weird and distant either. Try to find a balance that works for everyone.
Be prepared for your friendship to change, even if your friend said they were fine with it. Sometimes people think they're okay with something until they actually see it happening.
My friend Kate gave her blessing for her roommate to date her ex, but she told me later that seeing them together was harder than she expected. They worked through it, but it took time and lots of honest conversations.
Stories From the Trenches
I've seen this scenario play out so many times, and the outcomes are all over the place.
My friend Rachel started dating her college roommate's ex about a year after they broke up. The roommate was hesitant at first but eventually became really supportive, especially after she started seeing someone new. Rachel and the ex have been together for three years now, and all three of them are still close friends.
But I also watched a group of friends completely implode when someone started hooking up with their buddy's recent ex. The original friend felt betrayed, people started taking sides, and what used to be a tight group of friends became two separate groups that couldn't be in the same room together.
What made the difference? Timing, communication, and respect for everyone's feelings.
Other Options to Consider
Remember, dating your friend's ex isn't your only choice here. Sometimes the best option is to consider alternatives.
You could wait. If the timing isn't right now, maybe it will be later. There's nothing wrong with acknowledging your feelings without acting on them right away.
You could decide the friendship is more valuable than the potential relationship. This is especially true if you're dealing with a really close friend and you're not even sure how serious your feelings are.
You could be honest with your friend about your feelings without asking for permission to act on them. Sometimes just getting it off your chest is enough to help you figure out what you really want.
Or you could take things slow - getting to know the person better as a friend first. This gives everyone time to adjust and gives you a better sense of whether there's actually real compatibility there.
When to Just Walk Away
There are some situations where the answer is just no, and you need to be mature enough to accept that.
If your friend is genuinely hurt by the idea, respect that. Your friendship should be more important than a potential relationship, especially if you're not even sure how you feel about the person yet.
If the ex was abusive or manipulative in their past relationship, that's a huge red flag that goes way beyond your friendship. Trust your friend's experience and stay away.
If you find yourself more excited about the drama and secrecy than the actual person, that's a sign you should probably step back and think about what you really want.
Sometimes the cost is just too high. Before making any decisions, imagine yourself five years from now. Which choice will you regret more - not pursuing this person, or losing an important friendship?
My Take on the Whole Thing
Look, there's no universal right or wrong answer here. Every situation is different, and what works for one group of people might be a complete disaster for another.
The key is handling whatever you decide with maturity, honesty, and respect for everyone involved. That means being honest with yourself about why you want this, honest with your friend about your feelings, and honest about what might happen.
How you handle this situation - regardless of what you decide - will be remembered by your friends and will affect how they see you going forward.
Don't let anyone pressure you into making a decision you're not comfortable with. Whether that's friends telling you to "go for it" or others telling you it's "totally wrong," the choice is ultimately yours.
Just make sure you're prepared to live with whatever happens. Sometimes the best relationships come from the most unexpected places, and sometimes the smartest choice is to leave well enough alone.
Either way, think it through, be honest with everyone involved, and remember that good friendships are hard to find. Don't throw one away unless you're really, really sure it's worth it.