You Asked It

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Lesley answers questions about weirdness, sexual awkwardness, and flirting.

Do guys like weird girls? Would they ever date one? I’m weird. I admit it. It’s mostly the way I dress, and the kids calling me Google on account a how smart I am doesn’t help. But, I’ve never had a boyfriend. Are guys intimidated by my weirdness? Or creeped out by my awkwardness? I don’t really want a boyfriend now, and I definitely don’t need one, but since I’m in high school (as of yesterday) I should probably start worrying about that soon, according to teen movies. —Angela

Dear Angela,

No, I don’t think guys like weird girls. I think MEN like weird girls. I hope I’m not the first to tell you that girls mature faster than boys? Immaturity sleeps in the same bed as insecurity, fear, sarcasm, and all those other things that hurt our feelings sometimes. So yeah, boys can be intimidated by weird girls because weird girls usually reflect the thing that they lack, or are afraid to embrace: confidence, independence, courage—all the words that make us feel warm. And anyway, Google, you should be smart enough to know that teen movies are the TOTAL OPPOSITE of what being a teen is actually like. I’m not the teen-movie expert (kind of am actually), but isn’t it always the case that the weird girl wins out in the end? Come on now.

P.S. I didn’t have a high school boyfriend until I was a senior. Those were three very long, boring, obsessive years. My fashion icons were Andie from Pretty in Pink and Allison from The Breakfast Club. Does that answer your question?
P.P.S. That last line was sort of an insider joke about The Breakfast Club.
P.P.P.S. I’m a dork.

Maybe I’m just being melodramatic, but…why am I so awkward about sex? I’m 17, and I think about sex as much as a normal person, I believe. I’ve made out and done oral, but I’ve been single for a year now, so those things are kind of a distant memory. Now, I can’t imagine myself having sex. I find myself pushing away a lot of guys who seem to be sexually attracted to me because I feel threatened and uncomfortable. I can’t seem to get down this casualness that everyone else has about sex, but it’s frustrating to me because I’m not saving myself for marriage or anything. It’s starting to affect my self-esteem, because a lot of my friends and even a lot of people who write on Rookie seem to have that casual attitude about sex. And I just don’t feel like I’ll ever get over this awkwardness. What’s the deal?

Here’s what, homie:

1. I wonder if your dip in self-esteem came before your sexual awkwardness. The reason I say this is that usually when sex is all casual and non-awkwardy it’s because we’re super comfortable with our bodies and really understand how to get pleasure from just “whateves” sex times. Sounds like you just aren’t there yet.


3. I am trying to avoid this whole “you’re only 17 thing so don’t worry about it” answer because that’s such an annoying, condescending copout, and whenever I say something like that it’s usually because I don’t know how to answer a question.

4. I lost my virginity when I was 17. I was scared. It was awkward. It wasn’t like how all my friends had described it. It wasn’t even like how Judy Blume described it. It made me feel so much worse about myself because I didn’t like it and I thought there was something physically wrong with my body.

5. Now I am 32. SOMETIMES sex is awkward. Sometimes it hurts. Sometimes I feel so insecure about my body that I can’t relax. And not once, NOT ONCE, has it ever been “casual.” This is just my experience, which is important to note, because no one is right or wrong when it comes to matters of sex. Everyone has their own story, their own fears and deals and weirdness and sluttiness and all of it. There are SO many colors in the humping rainbow.

6. Let me also tell you that I too am super turned off by guys who act all “sexually attracted” to me. It’s just kind of cocky and gross and yeah, feeling put off by that is not weird. Unless I’m weird too, which is always a possibilty. But that would mean that there’s a million more weirdos just like us. So I guess that means that there’s actually no such thing as weird.

7. Did I just blow yr mind?

I have been dateless for all of the 15 1/2 years of my life. I guess it’s not a big deal, but it bothers me. It comes down to this: HOW do I effectively flirt with guys (and not seem sleazy)? —Anonymous

Dear Anony,

I think this is just a case of trial and error. I definitely didn’t go on a date for at least the first 17 1/2 years of my life. I tried by calling up guys and just talking and trying to be friends with them. It didn’t work, but I didn’t feel sleazy about it.

Flirting is just kind of hanging out more often than you usually would, so maybe just do that?

Worst answer,

If you have a question for Lesley, please send it to


  • GagaMcQueen December 6th, 2011 11:11 PM

    May I just take a moment to ponder the gloriousness of Rookie? You are modern, feminist, interesting, slightly dorky, fashion-forward, and just all-around awesome. Another great article!

  • Mags December 6th, 2011 11:38 PM

    You’re not awkward about sex. I think you’re perfectly normal. Sex was a really scary thing for me until I was 21 and finally felt comfortable going all the way. Sex can be great with the right person, but it can also be, well, not that great. Also, I think a lot of people who act or talk casually about sex might be bluffing.

  • Freja December 6th, 2011 11:56 PM

    The thing to remember is that there are just as many weird guys as weird girls. And ‘weird’ guys are the best.

  • sarebear December 7th, 2011 12:03 AM

    Is it just me or does anyone else want to save themselves for marriage?

  • julideeee December 7th, 2011 12:41 AM

    I find it so funny how most of these answers are incredibly useful to my life STILL in my equally confusing and awkward sex life in college. I agree with GagaMcQueen above in that this site is EXACTLY what I was missing as a lonely, quirky, and fashion-forward teen, but I’m so, so, so glad I’ve at least got it now! I’m a feminist, a dork, and fashionista all rolled into one, and I’m so glad there are so many others out there, too. Enough to keep this site rolling and to fill the comment sections, at least. Much, MUCH love to Rookie. Might be submitting something soon whenever I get the balls!

    • Anaheed December 7th, 2011 12:46 AM

      Do it now! You don’t need balls! We’re nice!

      • Tavi December 7th, 2011 12:48 AM

        Anaheed’s lying. I’m the nice one. She’s really, really mean.

      • Anaheed December 7th, 2011 12:56 AM

        Tavi actually does have balls. That’s why she never wears pants.

  • giov December 7th, 2011 5:45 AM

    my inner teen is so fucking happy I found rookie. these are all questions I still struggle with even though technically I somehow got past my teen years and managed to get laid at some point and got over a few things in the way. now I’m off to see my therapist, and it’s snowing. keep up the good work!

  • VictoryBelle December 7th, 2011 6:16 AM

    Don’t worry sarebear me too. There was an article before called never been kissed or something which was really good, we’re not the only ones!

  • Raebbies December 7th, 2011 10:04 AM

    I’ve always thought i was the weird girl, till recently people have started calling me interesting and cool. Even from guys..weird girls always win :)

  • Hedwig December 7th, 2011 12:52 PM

    P.P.P.P.S. I love you

  • I.ila December 7th, 2011 5:11 PM

    going to an all girls school, I am worried I will wind up on the 40-year-old virgin – the TV show. i am 14 and have never kissed anyone, never even held hands with a guy! i make myself so mad sometimes.

    • Dylan December 8th, 2011 12:15 PM

      I did too! It took me until 16 to have a Real First Kiss (ie, not a truth or dare or something)! Which felt super late at the time, but it is not. Its funny how normal that sounds now, after going through high school thinking I was so behind or something. Behind? Compared to what?!

      I used to set goals, saying, “you will have your first boyfriend by the end of first semester of sophomore year.” STUPID! I still haven’t had my first committed relationship yet, but it’s better than having had a boyfriend that sucks, just for the sake of being in a relationship. Some of my friends do that. They’re always bummed out. Laaaaame!

      It does make a difference not hanging out with dudes your age on a daily basis. All girls school was awesome in some ways, but I definitely didn’t come out of there thinking I had a “normal” aka teen-movie style high school experience with, you know, boys in the halls and stuff. Let’s just say, it’s been 5 years since I was 14, and the last 2 is when I got out of my “wah wah I go to an all girls school” rut and things got bettahhh! I used to get so frustrated with myself too, until I realized that most girls around me were in the exact same boat. Seriously!

  • Tavi December 7th, 2011 5:15 PM

    here’s the never been kissed article victorybelle mentioned — it’s one of my favorite things we’ve posted:’

  • YvonneVoo December 8th, 2011 7:55 AM

    Does anyone know of any other rookie-esque badass magazines or websites for girls/women? I love rookie so much, MORE THAN ANYTHING EVER, but three articles a day is not enough for me!

  • jkg December 9th, 2011 10:59 PM

    YvonneVoo- check out, it’s a great feminist/fun/informative site.

  • Rita December 9th, 2011 11:23 PM

    When I turned 16, a lot of my parents’ friends said stuff like, “Aw, sweet 16 and never been kissed!” Which made me furious because it was true.

    When I *did* have my first kiss about a month later, it was absolutely horrible. It wasn’t until I kissed another guy six months later that I realized that it was just because Guy #1 was just not a good kisser.

    I was a total late bloomer in pretty much all areas of sex, but trust me in that it does get better. You DO start to feel more comfortable in your own skin, and you get to know awesome guys (or girls) who are attracted to you for who you are (and yes, I know that sounds cliched).

    If I could go back in time and give my high school-aged self one piece of advice, it would be to stop freaking out that I was “behind” everyone else–everybody gets there at their own pace.

  • jscoexist December 11th, 2011 9:40 PM

    This site constantly assures me that I am not alone in… pretty much anything. No matter how many times I’ve been told that sooo many people have gone through the EXACT same things as me, I sometimes still doubt it – but Rookie Mag seems to always validate my life. There are so many teen publications that try to be so relatable, but there’s always some aspect that is totally off and skews every self-affirming thing they’ve previously said. This, to me, is completely relatable and applicable and makes me feel hopeful and good. Thank you.