Should I date my best friend's brother?

posted 9 months ago in Relationships
Post # 2
377 posts
Helper bee

Honestly, I don’t even think you should go there. You can’t fake attraction and you can’t force it. “Trying it out to see how it goes” will likely not end well and could cause harm to a lifelong family friendship.

Everyone is attracted to people for different reasons, but it’s still gotta be there. You can’t make yourself like him no matter how good looking he is and how perfect you are for each other, on paper.

Post # 3
883 posts
Busy bee

I’ve been in this situation before. I went on a date with a guy my coworkers encouraged me to go on. I thought the guy was a bit of a goober, but after our first date, he grew on me. After 2 1/2 years it didn’t work out, but it was the second best relationship I’ve had (fiance is #1). I would agree to one date, but don’t get romantically involved the first date. See how you feel the next day, and if you look forward to a second date. If not, you can remain friends without it being too awkward. Hopefully your best friend and his mom will be understanding if you don’t feel sparks. Maybe tell them up front not to get too excited; you just want a friendly first date to see if you’re compatible. 

Post # 4
557 posts
Busy bee
  • Wedding: September 2020 - Summer Camp!

Since you’ve known him gota while, would you feel okay saying, “hey, you’re a fantastic guy, but it’s still a bit hard to see you as anything but my best friend’s cool brother. I want to give it a shot though.” So that way he knows where you stand right now?

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