Name: Fallon
Age: N/A
Location: N/A

I was recently out with one of my best friends. She also happens to be an ex and my first…well everything. We no longer have relationship feelings for each other as I am with an amazing girl and she switched back to men. However, we are still extremely close and we still have issues with each other over dating mutual friends and such. We keep our sex life out of our friendship in an effort to respect one another and avoid awkward discussions. Anyway, we were out at a club and my older brother arrived with some friends. He proceeded to ask my permission to ask her out as well as advice for how best to win her over. I can’t help but feel awkward and I don’t want them dating but I know they could potentially make each other happy. What do I tell them? My brother doesn’t know of our past or that I am bi-sexual and dating a woman. My friend and I have so much between us that this could end disastrously in so many ways. I have so many angles of what is the right or wrong thing to do. I’m lost, oddly upset, and my conscience disagrees with my heart. Please help!!

Read the TLL Advice Panelists answers after the jump…

Lori Hahn

You don’t have a right to tell her who to see or not see – but, in fairness to your brother, you need to tell him you had a relationship and its significance to you.  It’s up to you to step up and set this right before someone you love gets hurt finding out another way.

Lori
Hahn at Home

Shanna Katz

Oh dear. This is quite a doozy.  It seems as though the simple answer is to tell your brother that no, you’re not ok with him asking your friend out, because you don’t know how him dating a close friend would affect all of your interactions, and because you’re nervous that if things imploded, you might lose a friend. I think, in general (orientation and history aside), that this is a reasonable request, keeping friends and family separate.

If he persists, and this is a big concern for you (which it might be), perhaps talk to your friend and share your concerns.  Explain that your brother has approached you, and you’d really appreciate her turning him down.  If she doesn’t understand your situation, then she might not be as good of a friend as you think she is.

And if all else fails, this might be the time (albeit not the best time) to explain to your brother about your orientation and/or history. Unless you choose to remain mum and just let this all be, which I highly advise against, as I can definitely see it affecting your friendship AND your relationship with your brother, should the two of them start dating.

Sending good luck your way,

Shanna
www.shannakatz.com

Dharma Kelleher

Dear Fallon,

My suggestion is to come out to your brother because odds are good he’s going to find out anyway. That doesn’t mean you have to tell him whom you’ve dated, including your friend.

That said, if you don’t want to hook your brother up with your friend, don’t. Just tell him that it feels weird to hook your brother up with your best friend. If they get together anyway, that’s between them. Don’t stand in the way. Trust the process.

Peace out,
Dharma Kelleher
http://www.dharmakelleher.com/

Tina-cious

Out of the Office

Tina-cious

Kelly Leszczynski

Fallon,

Unfortunately it seems that everyone, including your brother are starting off on the wrong foot. That’s not a good way to start any relationship. Reading your email also makes me SO THANKFUL that for the most part my brother and I have polar opposite taste in women.

Can you tell your brother about your bisexuality now? If you can I suggest you do. From what I read it seems like not every one is on the same page. Perhaps your brother is like the male version of you and he and your ex will have something special. No matter what the outcome I think you need to come clean with your family. If your brother is as good a brother as mine and he knows that dating her will upset you then he will back off. But if you see that they really have something you should think of getting over the pain for your brother’s sake.

Be honest and communicate. It’s the only way I see this working out well.

Kelly
Brain Clouds

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