Should I Set Up My Friend with My Ex on a Double Date?

Jake is stuck in that awkward zone where “helping” someone feels like it could quietly explode his entire friend group. It starts with Sarah, his good friend since college, saying she feels lonely and hasn’t had much dating luck.

Then comes the curveball, Sarah admits she finds Jake’s ex, Alex, really attractive. The breakup was amicable, they’re still friends, and Jake is tempted to set them up on a double date, with the whole thing disguised as just hanging out.

But the moment you hide that you used to date Alex, the double date stops being a cute plan and starts feeling like a loaded question with two people who could get hurt fast.

Original Post

So I'm (29M) in a bit of a dilemma. My good friend Sarah (27F) and I have been friends since college.

Recently, she mentioned to me that she's been feeling lonely and hasn't had much luck in the dating scene. Now, my ex-girlfriend, Alex (28F), and I ended things amicably a while back, and we've remained friends.

The other day, Sarah confided in me that she finds Alex really attractive and wouldn't mind going on a date with her. This got me thinking.

What if I set up a double date with Sarah and Alex, under the pretense of just hanging out as friends and having a good time? Sarah has no idea that I used to date Alex.

On one hand, I see it as a potential match that could make both of them happy. On the other hand, I feel like I might be meddling too much and that it could backfire, causing tension between them and maybe even ruining our friendship triangle.

I know things could get messy, but at the same time, it could also work out smoothly. So WIBTA for orchestrating this setup that involves my friend and ex?

The Double-Edged Sword of Matchmaking

Jake's dilemma reflects a classic conundrum in friendship: can you truly separate your past from your present? He’s not only weighing his friendship with Sarah but also the emotional baggage tied to Alex. Setting them up could mean rekindling feelings or igniting jealousy, potentially fracturing his relationship with both parties. It’s a high-stakes gamble that could lead to disaster.

Moreover, Sarah's eagerness to dive into a relationship with Alex raises questions about her own readiness. Is she genuinely interested, or is she merely looking for a distraction from her dating woes? The community’s responses likely varied based on their own experiences with similar situations, showcasing just how messy these dynamics can become.

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Sarah is lonely and open to dating, and Jake immediately clocks Alex as the “perfect” match even though Sarah doesn’t know his history with her.

The plan gets murkier when Jake considers keeping it under the radar, so Sarah shows up to a “friends night” with the person Jake already dated.

It’s the same kind of emotional bind as refusing to set up a best friend with an ex despite mutual interest.

The fact that Jake considers this setup after Alex became his ex adds an intriguing layer of complexity. It’s not just about matchmaking; it’s about balance and the risk of emotional fallout. Readers can relate to the tension of wanting to help a friend while grappling with lingering feelings for an ex. This situation taps into the fear of loss—what if things go well for Sarah and Alex, leaving Jake feeling sidelined?

Reddit users likely weighed in with divided opinions, reflecting their own experiences. Some might see the potential for a sweet love story, while others would caution against blurring lines that could lead to heartbreak. It’s this mix of hope and caution that makes the story resonate so widely.

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If Alex is still in the picture as Jake’s ex, that friendly triangle could turn into tension the second attraction turns into questions.

Now Jake has to choose between playing Cupid for Sarah and risking the fallout with both Sarah and Alex if the truth comes out later.

What's your opinion on this situation? Join the conversation!.

Why This Story Matters

This scenario highlights the intricate dance of relationships where past and present collide, making it a relatable conundrum. Jake’s predicament isn’t just about matchmaking; it’s about the emotional stakes involved. Can friendships survive when romantic interests intertwine? As we ponder this, it’s worth asking: have you ever found yourself in a similar situation, and how did you handle it?

Why This Matters

Jake's situation illustrates the tangled web of friendships and past relationships. By contemplating setting up Sarah and Alex, he's trying to help his friend while risking the potential fallout of hidden feelings and jealousy. Sarah's eagerness to date Alex suggests she's seeking connection, but it raises questions about her motivations—whether she's genuinely interested or just looking for a distraction from her dating struggles. This delicate balance between helping a friend and preserving his own emotional ties makes the scenario both relatable and fraught with tension.

He’s not just planning a double date, he’s gambling with the friendship triangle he’s already in.

Wait till you read about the AITA mess after someone set up their friend with their ex-boyfriend. See the love triangle drama.