Another week, another dating dilemma. Here’s a question from Jill, writing to us from the Lower East Side:

“I’ve gone out on a few dates with this guy, and now he wants me to meet some of his friends. For some reason, they all sound intimidating – he was really close with them in college and I’m worried they’ll disapprove of me. How do I impress them?”

There’s your first lesson, Jill: don’t be intimidated! You’re important enough that he wants to introduce you to his friends. That’s a big step and should give you a boost of confidence. If you seem really nervous, you may come off as being cold. Smiling goes a long way…and while you’re at it, be open to any and all conversation topics. You should be a participant, not an observer. This applies to guys too, DateSpacers! Women also seek the approval of their pack.

So here are a few ways to fit right in: During the day or night out, try to speak to all of his friends (individually, if it’s possible, and for at least a couple of minutes). When we’re meeting new people through a mutual friend, we often find ourselves falling into a trap where the entire conversation revolves around the antics of that mutual friend. By the end of night, no one has learned anything about the other person. So do your best to steer clear of this by making it a goal of yours to learn three interesting facts about each of them. Remember, if you go any further with this guy, you’ll be spending more time with his friends too. With that said, it’s ok to ask his friends a few harmless questions about his college days: Are there any funny stories you don’t know? What posters did he use to decorate his dorm room? Such questions show your playful side but also indicate that you’re interested in learning more about this guy.

Also (and this one works really well for men), if you get a chance, drop a compliment or two about your date in the conversation. Don’t make it obvious and don’t force it, but if you can occasionally mention (in context!) that there’s a certain quality you like about your date, the friends will be more likely to give you the thumbs up.

Here’s the last thing: don’t act like you’re too cool for school. Ok, to put it another way: try to act the way you normally do. If his/her friends think you’re putting on an act or are trying too hard to impress them, they’ll see right through it and wonder why their buddy is with a complete fake. It’s the oldest cliché in the book, but be yourself.

What are some of your strategies for hanging out with friends? Share some of your experiences in the comments section below.