[ManilaMarketingGuy]

So there’s this girl who dated my close buddy for like… four months tops. No cheating, no scandals, just fizzled. It’s been a year since they split. We’re all still in the same barkada, we still hang out, and tbh the vibes between me and her have been low-key for months. We finally had a real conversation last week and—lol—chemistry is chemisting.

Now I’m stuck between “shoot your shot” and “don’t be that guy.” Context: they weren’t serious-serious, my friend’s already seeing someone new, and I’d be transparent before anything happens. I’m not trying to be sneaky. But I also don’t wanna create weirdness in the group chat or make game nights tense.

Question for the council: Where do you draw the line? Is there an expiration date on the “off-limits” rule? If you’ve dated a friend’s ex (or had a friend date yours), how did you handle boundaries, the convo, the timing? Scripts welcome. I’m thinking I talk to my friend first, keep it chill, and set ground rules for hangouts—pero open to being told I’m clowning. 😂

Drop your takes and your personal rules. Green flags, red flags, deal-breakers. Convince me either way. Sana all drama-free, but let’s be real—what actually works?

34

[salty_sea_sara]

Dating a friend’s ex isn’t automatic villainy, but it’s delicate. If you’re going to do this, transparency first, timing second. A year isn’t ancient history, but it’s not yesterday either. Ask him straight, no banter. If he flinches, drop it. Group dynamics get weird, ffs. Also clock whether she’s using proximity. Green flag energy = everyone acts normal after. Otherwise, not my circus, mate.

22

[HopefulParalegal]

I’d treat this like a consent-and-boundaries conversation, not a casual heads-up. Tell your friend privately, early, and plainly: “I’m interested; nothing has happened; your comfort matters.” Offer him space to think and the right to say no to shared hangouts. If he’s okay, follow with a group message acknowledging it so no one hears it third-hand. If he hesitates or jokes to deflect, read that as a soft no and pause. Am I missing something? Appreciate any insight, but that script has kept my friend groups intact.

11

[Raw_TruthRex]

Short version: you want it because it’s nearby. Facts over feelings—your friend’s comfort matters if you still share spaces. If he shrugs, proceed. If he hesitates, abort. Don’t test the group vibe; it will fail under pressure. Stop simping for hypothetical chemistry. Real chemistry survives daylight and boundaries. Rex out.

8

[moonlightvoyager_007]

I’ve stood on this bridge before, wind in my ears and guilt in my pockets. What helped was naming it honestly: “I’m considering dating a friend’s ex, but I won’t if it costs the friendship.” He surprised me by blessing it, and the quiet after that conversation felt like clear night air. We set simple boundaries—no post-mortems about their past, no triangles, no gossip. Under the same moon, respect travels faster than rumors. If your friend can’t celebrate you, accept that answer gently and walk away.

22

[MulletAndManners]

Manners first, feelings second. Shake the man’s hand, look him in the eye, and tell him your intentions before you so much as plan a coffee. If he says fine, cool—keep the PDA off game night and don’t compare notes with the boys. If he balks, tip your hat and back out. Simple. Cheers from Bama.

23

[OsloOutdoors]

Group dynamics are like winter trails. One wrong step, and hello avalanche. Red flags = avalanche risk: secrecy, timeline overlap, friend still tender. Green flags: direct talk, clear boundaries, low gossip slope. If you go, pack snacks and clarity, and be ready to reroute if weather changes.

26

[budgetBackpacker]

Ask first, keep it tidy, no dramas. If messy, skip the trip, mate.

29

[neoncatwalk11]

Omg okay, nuance moment. If you’re gonna shoot your shot, do it face-to-face, not via the group chat like a chaos gremlin. Tbh dating a friend’s ex isn’t auto-yikes, but it’s high maintenance. Boundaries, transparency, and zero subtweets. If he’s weird about it, respect that and step back. Protect the vibe ✨.

16

[DataBeforeDates]

Per the data I’ve tracked anecdotally (tiny sample, big caveats), friend groups that survive “dating a friend’s ex” share three constants: explicit consent from the friend, a cooling-off period of 9–12 months, and no post-relationship autopsies. Risk spikes when secrecy enters or when the ex becomes a proxy for old conflict. If you can’t say, out loud, “I’ll choose the friendship if this hurts him,” don’t roll the dice. If you can, time-stamp the convo, set norms, then proceed with care.

28

[MatchmakerMomma]

Honey, I’ve hosted more living room mediations than I can count. It works when folks are grown. Start with kindness: tell your friend before she posts a selfie with you. Promise you won’t compare histories or make him the therapist of his own past. If he’s still tender, give it a season. If everyone keeps their dignity, this can be a blessing. If not, it’s a casserole for one and a lesson learned.

12

[DadBodIntellect]

The move isn’t “permission,” it’s alignment. You’re aligning expectations with your friend so the narrative doesn’t get written by silence. Say the quiet part loud: you value him, you see potential with her, and you won’t triangulate. If alignment fails, the cost is too high. Affection plus honesty > secret vibes.

29

[NormanJRyan54]

Back in my day we called this “don’t fish in your buddy’s pond,” but life’s messier now. I’ve seen it go fine when the men involved had real respect and no scorekeeping. I’ve also watched poker night die because folks tried to sneak it. If you proceed, make it boring—no drama, no commentary, no comparisons. Ask your friend plainly, accept his answer, and mean it. If the romance can’t survive that simple test, it won’t survive year two anyway. Your call, kid.

11

[BrokenAccent291]

I not judge, but secrets break groups. Ask first, be kind.

16

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