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Okay....so one of my friends...whom was in my wedding as a bridesmaid back in 2005....worked with her for 3 years as a dispatcher etc. etc. is encouraging me to go out with her brother who is about 5 years younger than me. His age (30) isn't bad to me.....but its the idea of dating the brother of a close friend that concerns me. It may or may not go anywhere.....if we went out....BUT...if it went bad....or did not go anywhere.....what would happen??? She would inevitably choose her brother over me and then I've lost a friend! IMHO.....I don't think its worth it! Her brother contacted me on that dating website......and I knew exactly who it was. He is sweet.....kinda cute....and seems responsible......HOWEVER.....I love my friend. She is pregnant and I want to be a part of her and her child's life..... and despite her encouraging me to go on a date with her baby brother..... I think its most likely a bad idea.

Thoughts? Have any of you ever ventured into uncharted territory and dated anyone basically socially "forbidden?" It kinda goes hand in hand with my rule of not dating co-workers. Don't crap where you eat type of thing.... IDK.

Yeah this is one of those "all or nothing" situations... proceed with extreme caution. It's good that you have her blessing but if it doesn't work out (especially if it ends badly)...

Yeah....that is what I'm saying....I think I'm going to avoid this situation at all costs. He's probably a great guy....but its not worth losing a friend.

THen go ahead and tell her just like that "Your brother is obviously a great guy. However, I know that even relationships with the best intentions don't always work out. You are one of my dear friends and I would hate for it to end if things with him don't work out. I appreciate that you're looking out for me. Don't hesitate to send me other good men!"

I thought you were taking a break from dating?

I think you've made the right decision Shelly :)

I personally would never date a close relative of any of my friends. Same goes for dating at work, its a disaster waiting to happen.

Lots of people are able to navigate these situations - I am not one of them. Especially as I get older and my friends are actual friends, not just party buddies/acquaintances.

I say trust your gut on this one - could you navigate it?

It kind of sucks though - don't most people meet through work or friends of friends? Isn't that the best way to meet people? This friend sounds particularly close though so I would be loathe to risk it.

The friends brothers friends? Go for it.

I thought you were taking a break from dating?

I am! This situation fell into my lap and was a big fluke! I would have never responded to his email on the dating site but I knew him and consider him a friend. I should have just ignored him but then it would be awkward because it would have been read as I blew him off. Just seemed like a fine line. I'm going to have to deactivate my account. But, I told him that I'm taking a break and that dating is just too hard for me right now with trying to find time to date and being a single mom with a toddler. I told my friend the same thing. I hope she understands but I know when to walk away.

I made plans instead for next Friday to go to a movie with Piper's Godmother (my friend of 29 years) instead. And, my best friend is awesome....and is planning a birthday party for me in July! She's got a pool and we are going to go get Mexican food on half price margarita night! WOO-HOO! Life is sweet and I don't need a man to make it that way!

[This message edited by She11ybeanz at 7:41 AM, June 6th (Friday)]

Why do you think it's a bad idea? Is there any other reason, except for the part that he's your friend's brother?

"End badly?"

How?

What are you going to do to him that is so bad that your friend would choose her brother over you?

If he likes you, and you don't like him, he should respect that and move on.

We're adults here. Sometimes relationships don't work out. It shouldn't affect anyone's relationships besides you and her brother.

My significant other is the brother of a good friend.

At the time, I was asking select friends and colleagues if they knew someone that they thought might be a good match to let me know about them. I actually consider this to be a good strategy, because it's someone who knows you and they know the other person.

Situations like this can be awkward but if everyone is capable of acting like an adult it doesn't have to be catastrophic if it doesn't work out.

I dated a guy at work, way too soon after I split from X. Things didn't work out, and yeah it sucked at first because I felt rejected. But now we're just friends again.