1) Don't date your best friend's brother.
2) Don't date your best friend's (same friend in #1) serious boyfriend's best friend.
Did you get all that?
Why you ask.....because you will see these guys a lot after you break up, causing great moments of awkwardness. Granted it does get better, but still a little weird. For instance when your best friend marries said boyfriend and asks you to be in the wedding + two guys you dated also in wedding = AWKWARD! Thankfully, I didn't walk down the aisle with either of them, but what a fun limo ride when a random conversation about being friends with girlfriends after you break up takes place. Seriously?!
When these friends are leaving the country for two years and have a going away party, you go and see....former boyfriend A with wife and baby on the way and former boyfriend B with wife and newborn and even though you try to avoid them you end up having to say hi....by yourself....because you are single = AWKWARD!!!!
And does it seem awkward for them??? of course not! I think the awkwardness is more that I want them to see how happy I am with my life too. I just don't have a spouse and kid to prove my happiness. I have a table full of friends, a new niece(!!!!!!!), a new job, and um....new boots. They did see the boots. Oh this need to prove myself to others....silly sanguine.
The moral of the story: if you ever get asked out by a good friend's brother followed by a good friend of the guy she is with, think long and hard about what that will entail.
It could be worth it, then again maybe not.
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