I have this friend. I'll call her Lorelai because she's a Gilmore Girls fan and loves coffee and talking fast. She's funny and cute and totally has her shit together- owns her own place, good job, cool hobbies, etc. Lately, though, she has been down in the dumps about her lack of man.

Enter my other friend, who I'll call Emma. She has a dude friend that she thinks would be perfect for Lorelai. So Emma throws a party and invites Dude and Lorelai. We didn't tell either of them about the set-up because that would be awkward. Lorelai gets nervous under that kind of pressure and scrutiny. It was my job to get Lorelai to the party, just tipsy enough to be flirty. I did my part, but then… the plan fell apart.

Have you ever tried to get two people who don't know each other to talk at a party where they both have separate friend groups? It is hard! Or maybe I'm just TOO subtle to effectively be a matchmaker. We ended up leaving without the two of them having any meaningful interaction at all. I am no Emma Woodhouse or Cher Horowitz.

I think if we try again, the group needs to be smaller to encourage conversation. And maybe the event needs to be on the weekend, so that Lorelai won't tired.

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Have you guys ever successfully made a match? Any tips?