photo by I Love Egg

Dear Em & Lo,

There is a man who likes me, and he’s the type of man who every woman would want to have. He’s funny, kind, charming, and such a gentleman. The problem is, he’s my best friend’s older brother. He told his family that he’s had feelings for me for some time, but never acted on them because I am his sister’s best friend. His family, including his sister (i.e. my best friend), said it was okay and gave us their blessing; they say we should go for it ’cause they think we will make a good match. I would love to date him, and get to know him more — we do have a lot in common and he would be a great catch.

BUT, I really don’t want to run the risk of ruining my friendship with his sister — we’ve been best friends for over ten years now.  His family is like my second family, we are very close — and I don’t want anything ruining that either. What if we did date, broke up and things became awkward or we had hard feelings about the breakup?

I also have my plate full with a new job and going to school. He understands, says he will wait, and maybe on our days off of work, we can see each other. I am 24 years old and he’s 32, and we’ve been in our share of relationships. When I found out he liked me, I was happy, but thinking about it for a while now, I’m not so sure. What would you do about this?

— All in the Family

Dear AitF,

Go for it! This guy sounds great, his family sounds great, you have their blessing, you’re into it — how can you not go for it? You’ll forever wonder “what if?” And if it works out, these people could ultimately be your in-laws! You can’t pass up an opportunity like that out of fear that it won’t work out. If people lived their lives trying to avoid all hurt and pain, nobody would leave their house!

That said, you should just assume right off the bat that you are eventually going to break up — just as both of you have with every single other person you’ve dated before. The stars have to be aligned just so for two people to both decide they never ever want to break up (and even that’s no guarantee it’ll last). Plus, you’re still very young: you still might have some dating around to do.

So, by assuming you’re eventually going to break up, you two can seriously set some ground rules up front about respect and boundaries, should things come to an end: like responsible parents going through a divorce, you need to commit to keep things amicable; no cheating; no talking to other members of the family about the details of the breakup; no bad-mouthing the other in front of the family; and really try to take that breakup cliche about remaining friends seriously. Then hopefully, after some time has passed, you two will be able to joke about that time you guys dated at the family’s holiday party.

If this family is as cool and close with you as they seem, then even if you eventually break up, it sounds like he’ll be able to abide by the above rules and won’t be a jerk about it — and even if he tried to be a jerk about it, it sounds like his family wouldn’t let him get away with it, out of loyalty to you. It also sounds like you really respect all these people, which will probably help you be a better girlfriend — and a better break-upper, should it come to that.

With our blessings,
Em & Lo