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A friend of mine really wants to date me, but I think it would be a terrible idea. How do I let him down gently?

Anna: Friends always think that it’s a good idea to date other friends. In some ways, it makes sense: You probably have a lot in common; you may have the same sense of humor; your friends will approve of him. If you have a good friendship, and you are attracted to one of your friends, why wouldn’t you put the moves on him? But I often find that this kind of feeling isn’t reciprocated, which creates all kinds of awkwardness within a group of friends. The best course of action is to be straightforward about your feelings: Tell them that you are not interested in anything other than friendship. Emphasize the fact that while you think that they are great, you need a little more than just friendship to have a good relationship, and you two just don’t have that “spark.” I would also add a line or two about how you don’t want to create tension between your friends, and you hope that they don’t hate you too much for this little rejection. An “I’d hate for this to ruin our friendship” will do.

Chris: Here’s the reality about most of these situations: There is no way to let your friend down gently. You owe it to your friend to be completely honest with him, and to do anything else is unfair to both of you. When and if he asks you out again, you have to let him know that you are not interested in him that way. Be warned though, you’re likely to be in a rather stressful and awkward situation with your friend afterward. It takes a lot of courage to admit you have feelings for someone, and it is harder still when that person is one of your good friends. You are, essentially, rejecting him, and everybody deals with that differently. Like Anna said before, make it clear that you don’t want things to be awkward, but you should probably give him some time. Feelings don’t just disappear overnight. Tell your friend that it is in his hands, that you are there for him no matter what and are ready to talk to him when he is ready.

What are good lines to use to pick up girls?

Anna: There isn’t any sure fire way to pick up girls, but there are a few things to do that will make your chances better. If you have one particular girl in mind, try to get a mutual friend to introduce you. She’ll see immediately what you have in common, and hopefully you’ll have a foot in the door with her friends. Keep in mind that a girl’s friends are very persuasive: If you’re leaving with a girl, and they don’t like you, they could pull the “you’re not yourself right now” card at a party, and end that potential hookup quickly.

Generally, I feel that the people who have the most success picking up chicks are funny and generous. Cracking a few good jokes goes a long way. In terms of being generous, there isn’t much to say. If the opportunity arises, offer to pay for her entrance fee into a party, buy her a drink, or handle her Bart Mart munchies. Oh, and please, please remember to have good hygiene.

Chris: Anna has done a great job giving the DOs for picking up a girl. However, it might also be beneficial to know the DON’Ts.

Rule #1: The aggressiveness of your pursuit should be inversely related to the drunkenness of the girl that you are pursuing. Doggedly pursuing a drunk girl just isn’t cool. If you can’t pick up a sober girl, then for damn sure you shouldn’t be picking them up drunk.

Rule #2: Don’t pursue any one potential girl too avidly in a short period of time. There’s nothing weirder than being chatted up by the same person over and over again in one night. When a girl rejects you the first time, that’s usually pretty indicative that she won’t be interested in you at all for that night.

Rule #3: Avoid getting plastered. There’s nothing as unsexy as being hit on by a guy that thinks he’s being smooth but is really just a drunken mess. You need to keep your wits about you to get a girl.

Finally, stay calm and be relaxed. Don’t treat this like a chore; it should be fun.