Dear He Said/She Said,

I just got out of a long-term relationship. I feel that I am ready to start dating again and I already have a few options. The one “option” I am seriously considering happens to be my ex-boyfriend’s brother (oopie!). Obviously, I am a little hesitant about this. But I’ve been really attracted to him since I met him last year and I think he feels the same way about me. What in the world should I do?

-Keeping it in the family

Dear Keeping it in the family,

Oopie, indeed! I must say, that is rather scandalous of you, but if you can’t help what you’re feeling inside, why not?

If you’re still friends with your ex-boyfriend make sure that you, at least, discuss this with him. I’m sure you don’t want to surprise him by showing up at his family reunion with his brother, that might be kind of rough and we might then be faced with a new version of sibling rivalry.

If you want to keep it in the family and date his brother, go for it. Who are we to judge and say no to that? If his brother knows how to work it better than your ex, I don’t see any reason why you should torture yourself. You’re young and life has so much to offer, explore what’s out there and get the best of it.

Whether it’s his brother, his uncle, or his nephew (preferably over 18, otherwise we’ll be discussing statutory rape next week) go for it. Have fun, but BE SAFE!

-Vee

Dear Keeping it in the Family,

Since you have been out of the “dating loop” for a while I’m going to let you in on a little secret-it’s never a good idea to date brothers, good friends, or your ex’s best friend. By doing any of these things you may end up in an awkward situation. I’m not saying that these things never work, but I’m saying that right now it may be difficult to start dating under such complex conditions. If you are really interested and know that this guy is going to be worth your trouble, ask your ex-boyfriend how he feels about this situation. If you play your cards right you should be able to be happy dating other people, but also keep the friendship of your ex. If you’re ready to move on and maybe lose one of your good friends (your ex-boyfriend) then go ahead and see what happens with your ex-boyfriend’s brother, but I’m not promising a pleasant result.

Good luck in your new single life. Just remember to be safe and take into consideration other people’s feelings before jumping into anything.

-Andrea