Essentially I live with 2 women, who are very attractive (9-9.5) and have a wide friend base of other attractive women. When we go out, we like to make the best of it because we are busy, so we've started winging for each other. We've done it about four or five times now and here's common sticking points that I run into.

  1. "Do you always have your roommates talk to girls you think are attractive?" - So far my responses have been "No this is the first time" and "You'd probably think I was a creep if I just randomly talked to your group." Neither have positive responses.

2."Why don't you and your roommate date?" This has come up a few times cause we are both single. I usually say something around the lines we are just friends, but that usually gives an odd look. Any other ideas?

  1. I feel like sometimes the girls are little insecure because my roommates/friends are so attractive. I don't place looks as the primary incentive to get to know someone, I like to date more on where they are professionally (medical + dental girls are super hot in my book) because I am looking for a LTR so i will date down some in the looks section if they have other qualities i find desirable. Is there anyway I could diffuse this or make them feel more comfortable? Would lots of compliments help?

  2. Is there such a thing as too much social proof? It's not uncommon that it'll be only myself and 4 or 5 extremely attractive girls. I know that's supposed to be a good thing, but sometimes i think it's intimidating to girls i want to meet. Occasionally other guys will be with us, but we are always out numbered.

  3. Sometimes when one is opening up to a larger set of girls/mixed group (4-5), it's hard to get them to me. Are there any other good openers to insert myself in their conversation besides saying Hey, who are your new friends?

  4. How to ask for numbers? Lately I've been using we are having a party this weekend or tomorrow. It usually works, but I need other options.

When I am winging for them -

I have tried two things when opening to guys for them.

  1. Is just to say hey, introduce myself, have them introduce themselves. I've only done this when the guys are alone or in sets of 1 or 2, so I'll cut right to the chase to demonstrate value and say my roommate thinks they are attractive. That usually changes the tide of the conversation very quickly, but sometimes guys are too aggressive when they meet the girl and makes them feel uncomfortable. Any ideas on how to put this less bluntly?

  2. The other method, which we used if it is a larger group is walking up and asking if they go to a school round the area, there are many, so this works well if they are younger appearing. I usually only have to carry on the conversation long enough to get names before the girls follow me and ask what I'm doing and I'll introduce them to the guys.

But if the guys are older and in a group of 3 or 4... I don't really know how to open, any ideas?

Any ideas in general how to open to random guys in general? The more I can wing for them, the more they'll do it for me.

I'm very open to any other ideas or suggestions you guys have. This is a great opportunity to get my feet wet and talk to a lot of women, I want to make the best of it.