Dating your friend sister
You've been spending a lot of time with your bud's little sister and now you're realising hey, she's actually really kind of hot and awesome.
But you need to take things one step at a time here.
If possible I'd like to be closer to her but I don't want to risk losing these relationships because they each are a really big deal to me.
Thanks for reading, Average Crate Box Believe it or not, this is actually a common occurrence, ACB.
Today it's all about walking the line between being the cool guy and the pushy jerk. Hey Doc, I've been a fan of your friendly but stern advice since I first read your column but to be honest I never dreamed I'd write in.Again, I'd say that a head's up isn't necessarily warranted unless and until things are starting to get serious; if you two just go on a date or two before realising that it's not really going to work out, then you've invited a lot of excess drama for no reason.But if it's looking like you two might have an actual want to tell him. "Hey, I just want you to know: your sister and I've been talking a lot lately and we've been getting pretty close. He might be weirded out because of the way the two of you have had mutual discussions about all the ways you want to get your freak on with different women and it's completely different when it's his around him.It gets people excited and that excitement turns into arousal very easily.
Moreover, you've got your friend talking you up to these women; this is the best possible form of advertising short of having an ex-girlfriend vouch for you.
First things first: until she's back in the country, it's kind of a moot point. I think you're awesome and you're a great friend and I'm glad we've been getting close.