Should I Have Set Up My Friend with My Crush Without Knowing Their History?

A simple matchmaking favor turned into an awkward little mess for one Redditor, and it all started with good intentions.

The 29-year-old OP thought his friend Emma, 26, and his buddy Alex, 28, would hit it off, so he introduced them after hearing Emma wanted to date again. The problem was that Emma and Alex had already gone on a few dates years earlier, something OP did not know when he set up the coffee meet-up.

Now he is stuck wondering whether he crossed a line, even though he was just trying to help. The comments have plenty to say about that.

Original Post

So I'm (29M) and I have this good friend, let's call her Emma (26F). Recently, we were hanging out, and she mentioned wanting to find someone to date.

Now, here's where things got a bit messy. I know this guy, let's call him Alex (28M), who I thought would be a great match for Emma.

They have similar interests and personalities, so I thought, why not set them up? For background, Emma had never mentioned any past relationships or crushes, and Alex is a nice guy who's been single for a while.

So, I casually mentioned Emma to Alex, and he seemed interested. I thought I had done a good deed by potentially setting them up.

However, after setting them up on a casual coffee date, things took a turn. Emma later confided in me that she had actually gone on a few dates with Alex a couple of years ago, but it didn't work out due to differing priorities at the time.

She hadn't told me about their history because she didn't think it was relevant. Now I feel torn.

On the one hand, I genuinely didn't know about their past, and I was just trying to help. On the other hand, I unknowingly set up my friend with someone she had a history with, which could be awkward for both of them.

So, would I be the a*****e for setting them up without realizing their dating history? I honestly don't know if I crossed a line here.

What do you think?

Comment from u/GamingFanatic88

Comment from u/cat_lover42

Comment from u/coffee_holic

This gets messy like an AITA where someone set their crush up with their friend, after they already knew each other.

Comment from u/AdventureSeeker99

Comment from u/throwaway_123

Comment from u/rainbow_dash

Comment from u/musiclover77

Comment from u/bookworm_girl

Comment from u/random_user789

Comment from u/pizza_addict

How would you handle this situation? Let us know in the comments.

Think you had a “set them up” problem, check out setting your friend up with your ex without telling him.