I seem to have a problem getting a woman; maybe it's my shyness that makes them not want me. I'm 23, and my last relationship was in 2004. You could say I'm an "Internet geek"- the quiet, conservative type who doesn't really make a move. And it's killing me, partly because I don't know how to accept rejection, whereas some guys don't care if they get rejected.
Worse, I'm clueless about what to say. Whether it's at school, in the gym or at the club, I seem to lose my chance. My friends (both male and female) tell me that I'm attractive and very good-hearted, but I feel that I'm lacking confidence and in need of a boost.

- Missing Out

You could also say Bill Gates was an Internet geek – and it’s served him well. It’s good news that you have both female and male friends, and they find you an attractive person; it means you have every likelihood of being able to have more romances in your life.
What’s needed are some social skills, including ways to converse. Practice on your pals, by opening up new topics rather than slipping into your usual chats. Read the newspaper for interesting tidbits, observe your surroundings, and push away from your computer to try something new – rock climbing, snowboarding, whatever. Now you have something to be enthusiastic about in conversation. Don’t believe that other people handle rejection well; they’re just better bluffers than you. But you may be overreacting – when a woman doesn’t connect with you at “Hello,” that’s not a rejection; it’s a poor fit. Be more selective yourself about who seems interesting and worth trying to get to know.

My best friend and I are very close but she has one failing that drives me up the wall... she's the nosiest person I know. I get angry when she tries to find out information about me. I've been able to deflect some questions but sometimes my anger erupts, I'm short with her and I end up hurting her feelings. That just makes me feel badly.
How do I get her to mind her own business without harming our friendship? Is there a way to respond (perhaps with humour), to deflect these probing questions?

- Put Off

Honesty is what’s supposed to happen between best friends. So tell her up front: You prefer some privacy in your life and don’t want to share every detail. Period. It’s counter-productive to worry about “hurting” her with this direct statement. After all, you must hurt her more and perplex her with your anger, when she doesn’t get it that you want her to stop digging.
Humour? It’s one of my favourite relationship tools, but in this case, she needs to hear straight up that you two have different interests in your personal life – hers is merely curiosity while yours is your integrity to protect.

I'm a 15-year-old girl who likes this guy, 16, who broke up three months ago with his girlfriend. She used to be my friend and now is distant because she's suspicious of me liking her ex. I talk to this guy on the phone, he flirts with me and we danced at a party together. I feel like he's giving me all these signs, yet when I talk to him about relationships and whether he's ready for a new one, he says no. I feel like he's leading me on, but I really like him and would like to start a relationship with him.
How do I make him like me and open up?

- Determined

The worst way to go after a guy is to pressure him when he’s already said he’s not ready. Phone chat and one dance are not major signals that’s he’s interested, they’re just what’s natural between friends. Don’t lose that advantage of being good buddies by trying to “make” him like you. Relationships can be intense and break-ups upsetting during teenage years, so he’s smart to give himself time to chill, flirt a little, and not get involved again quickly. Back off.
As for your friend who’s his ex, well, that’s the law of the dating jungle. If you’re obvious about going after this guy so soon, you risk your friendship with her. Seems to me this is a good time to cool off yourself and assess your friendships rather than fixate on winning over someone who’s not that interested.