dear erika,

Your Question: Hi, I'm not sure what I should do. You see, one of my friends asked me out on a date and I really actually like him, and I know he likes me, but I'm scared. I know, I know, I shouldn't be scared, but there are many
reasons I'm scared...

1. His image isn't quite all that great. It totally didn't matter when we were friends, but when he asked me out my friends laughed. They told me I could do better and I could find someone HOTT. In my mind I want to give him a chance, but my friends are getting inside my head. If they were my real friends they would back me up, right? I really want to give him a chance because I really like him as a friend, he is
so sweet, smart (but he tries not to be), funny, outgoing, truthful (he's never lied to me), he's been my best friend for a very very long time... Looks have never matted to me before so why are they in my
mind now? Is it just because my friends got inside my head? Is it because I like him and I'm scared?
(I'm also scared because)

2. My last two relationships ruined friendships. I was best friends with one of them since pre-school and the relationship ended our friendship. I was best friends with the other one for six years and the relationship ended our friendship. I'm afraid that this relationship will end our friendship. Am I thinking too much about this? Should I ignore my friends, go for it, and see what happens? How should I ask my mom if I can go on a date? (I've never asked anything serious before.
I would like to thank you for your time and I hope to hear from you soon. I am sorry for leaving so many questions. My head and heart aren't connected right now for some reason.

Thanks, greenlay

Dear Greenlay,
This best friend of yours sounds completely awesome! Funny, sweet, smart, and loyal? What more could a girl want in a boyfriend? Well, according to your friends, a girl should want someone who registers higher on the hotness scale. But you know what? Your friends aren't looking to date him, so that's beside the point. The question here isn't whether you should listen to your friends; it's whether you have enough chutzpah to stand up to them and let them know that these qualities of his make him hot to you. The truth is, people get hotter once we get to know them better -- personality can take a so-so-looking guy from meh to oh yeah quickly. There's no doubt that if you do end up going out with this guy, your friends will begin to find him hotter too, once they A. get to know him more and B. see how well he treats you. So it's up to you to go for your true feelings and trust that your real friends will see the light.

Once you've worked to get your friends out of your head and rep your feelings, you've got to contend with your fear of ruining yet another friendship by taking things to a romantic level. Since you've been burned twice by dating former best friends, it's totally understandable that you would be hesitant when thinking about categorically moving this guy from friend status to boyfriend status.

The good news is, you've got experience on your side. So sit back and reflect on what went wrong with these former friend-turned-boyfriend relationships. Maybe the two of you stop clowning around and having fun once your relationship got serious. Or maybe the two of you stopped treating each other as well after a while, once you no longer had to work for each other's affections. Whatever the case, it's totally worth examining to figure out what went wrong. After your moment (or, let's face it -- days or weeks) of reflection, gear up to talk to your friend/potential boyfriend. Let him know your fears and hesitations about entering a new realm in your friendship. Tell him what went wrong in the past and make sure you both will work together to ensure those kinds of road bumps don't arise in your relationship. If this guy is as truthful, sweet, and smart as you say, the two of you should be able to share fears and hesitations and sort out whether you're truly ready to take your relationship to the next level.

Finally, if you do decide you want to date this guy, you'll have to flat out ask your mom for permission. The tried-and-true way to negotiate these first dating rights is to ask your mom point-blank -- at a nice Zen time when she isn't busy or distracted by something else. (Maybe when she's reading a magazine on the deck?) And be sure to show your mature side by offering to introduce the guy to your mom ahead of time, suggesting a reasonable curfew time, telling her exactly where you'll be going and with whom, and by sharing your intentions and views on how intimate you do or don't want to get with this guy.

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Erika Stalder is a San Francisco-based writer who contributes to "Wired" and "Edutopia" magazines and worked with the International Museum of Women to produce the "Imagining Ourselves" anthology. She wrote Zest Books' The Date Book also coauthored 97 Things to Do Before You Finish High School .