You Asked It

Just Wondering

Advice on hooking up, internet friends, and masturbation.

I’ve become pretty disenchanted with relationships, but I really like the physical aspects of dating. Is it OK to just hook up with people until I feel more confident about who I am and whom I’m looking to spend the rest of my life with? —Lily E., Decatur, Alabama

The rest of your life, girl, damn! That sounds like a lot of years that you’ll be spending with this potential future boat o’ dreams. I imagine that it will take a WHILE to find somebody worthy of so much of your time. I also imagine that you will sometimes feel the great urge to attach your mouth/body to the mouths/bodies of others during this waiting period. (I imagine this because it’s exactly what you wrote. Pretty perceptive of me, I know. Bring me your hardest advice questions and I’m pretty much guaranteed to spew out all manner of beautiful insights like this.)

Before we get into the ostensible matter at hand (and mouth/body) here, allow me to address the REAL Just Wondering that you hid in this question all coy, like, “This is the idea I really want someone to talk to me about, the soulmate thing, but I’ve been let down before, so I’m gonna couch it in this lascivious ’n’ devil-may-care sex query, lest people think I am a herb who wants to feel a thing.”

Look, dude. I absolutely believe in true love. It’s the thing I believe in maybe above all other things in life—you can find it in friendships, in artwork, in sunny pockets of the afternoon where you just feel lucky to be hanging out in the world, and, of course, in romantic partners. I wonder if I could ever spend my whole life with someone, if they were dope enough. Probably. I also think I could, and will, spend stretches of my time on earth with other long-term partners, exploring, you know, the “physical aspects of dating” (YOW). It’s OK to believe in, like, Plato’s Symposium thing, where the playwright Aristophanes talks about how we’re all half-people casting about for the missing double that will complete the erector set of our selves—it’s the theory that everyone has a missing partner that fits them perfectly, in all places, like wearing a flawless bodycon dress but better, since it’s UNDYING, WHOLE, ENDLESSLY ROMANTIC LOVE. That’s like at least 12 flawless bodycon dresses, in terms of feeling good, probably.

Of course, it’s fine to not believe in a one and only. And you don’t have to pretend—and I’m not saying you’re doing this here, but others reading it might be, and I did it myself, once upon a time—that you do believe if you don’t. In my pre-18 years, I used “not having met the right person” as an excuse for wanting to put my mouth/body to extensive, diverse work because I didn’t want people to think I was a skank (no such animal, by the way): “I just haven’t found the THE ONE! That’s why I have to make out with this incredible-looking bohunk/Betty whose chest I’m already groping! SIGH!” Just kiss (or whatever) him/her/them, darling-thing. You don’t have to explain a thing to anybody. It’s five thousand percent fine.

I guess this brings us to the body encasing the heart of your question: Yes. Make out with whomever you like. Just make sure you’re doing it because you want to, not because you feel like you’re supposed to or like you’re rotting away for not being with someone you actually adore instead of whatever rando is around to make you feel like you’re “normal” for being Young Person Having Kiss Experience! High School Party!

Since you mentioned building confidence, I’m gonna mention it too (those incredible advice-giving instincts kicking in again, I know, PayPal me a high five or something): The phrase “until I feel more confident about who I am” seems to me to be an expression of almost terrifyingly on-point acumen in re: understanding that you need room, as a young person, to grow and shred at will, and that sometimes that process involves experimental games of TONSIL HOCKAY. If this is what you meant, I should be PayPal-ing you, because that’s amazing, and: yes. BUT. If you meant “until I hook up with enough people that I feel ready to settle down without some sense of missing out on a broader spectrum of bods and babes”…HA, just kidding, that’s also totally fine! Do it up. Wait, wait, though: On a serious note, if you’re saying that you need to hook up with people IN ORDER to be confident that you are an attractive, rad person, that’s where I cock my head a little. You don’t. You already are. I know you know that—I’m just making sure. (And if you don’t know it, GET TO KNOWING IT, SERIOUSLY.)

Anyway, I love you a lot, and I’m wrapping up, but finally, it doesn’t sound like you’re all that “disenchanted with relationships” from where I’m typing this to you (empty bathtub—long story). Based on the last part of your question—that “rest of my life with” business—it sounds like you believe in true love just as fervently and ferociously as I do. You will find amazing people everywhere, if you make yourself available to them—people who will hang for the short-term (HOOKIN’ UP, HOOKER!!! WOO) and the long-term (Aristophanes, if you want). Do whatever you feel is right, and OF COURSE it’s OK so long as you’re safe and respectful of yourself and other people. I’m sorry if someone hurt you, or something. Fuck that person, for real, and you can tell them I said it. Now go have a great time. Yes! —Amy Rose


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  • soviet_kitsch May 20th, 2014 11:53 PM

    lola, i’m SO glad you pointed out that penetration doesn’t have to be a part of sex. that goes overlooked quite often! there are so many ways to have sex that don’t involve inserting this into that

  • Anna May 21st, 2014 12:34 AM


  • emseely May 21st, 2014 12:51 AM

    queen ARS strikes again

  • maskedcat May 21st, 2014 1:46 AM

    Hey Olivia- If fingering yourself hurts then it might be a good idea to talk to a gynecologist. (Especially if inserting a tampon also hurts – assuming you’ve started your period and tried tampons, obvs.) What you’re describing sounds a lot like me at 14. I tried talking to my mom but she didn’t really believe me so I figured I must be doing something wrong. I found workarounds for masturbation (friction!!!) but when I finally started having sex it was crazy-painful. I eventually found a good doctor and got diagnosed and treated but I could have avoided a lot of unnecessary pain if I’d stuck up more for myself and made my parents (and doctors) take me seriously. It can be hard to talk about such a personal thing, but it’s totally worth it to find out if something’s wrong.

    For what it’s worth – two fairly common conditions that can cause the kind of pain you’re describing are vulvodynia and vestibulodynia (VBD). They’re both conditions where some of the nerves ‘down there’ aren’t working properly and register what should be a nice touch as really painful. They get misdiagnosed (or ignored) a lot and women and girls lots of times are told it’s ‘all in your head’. It sounds a little scary, but they’re totally treatable! I’m not trying to diagnose you or anything – I’m not a doctor or anything and you know your body best. If this doesn’t sound right, ignore me! Just remember, as long as you’re gentle, it should never hurt to touch yourself down there. If something does hurt you should check it out and if no one listens, keep trying – you’re worth it!

  • RatioRae May 21st, 2014 4:47 AM

    Hey Cass, I used to feel the same way all the time. It didn’t help at all that this friend and I eventually got into a big fight and she started writing really mean things about me online. Eventually, I just got over it because I realised that although we shared some of the same traits, there are so many other things that makes us unique. Find those completely unique traits and you will shine! Also, greetings from a fellow Malaysian. ;)

    And to anon, it’s not that hard, sometimes you just have to reach out! It’s ok if you don’t have common interests at first. I only started getting interested in certain things after reading about the passion others have about it. Feel free to hit me up on my blog or whatever, I love making new friends! :D

  • Vlada May 21st, 2014 5:24 AM

    Love this post as always, Amy your writing is unbelievable! I love how you present you point of view, and the advices you give, so thank you for that.
    Hello Hazel!!! The question you answered is one that I’ve asked myself many times. This friend I have wouldn’t stop “copying” me and at first, I felt like she was stealing something from me. Then, I realized that she happened to like my style and how I did things, she just embraced my methods because she thought they worked and I’m glad to be someone elses example. She didn’t copy me, she thought that I was cool enough to do some things they way I did them WHAT A HUGE COMPLIMENT!
    Thank you Lola for being so open about an issue that people seem to think is awkward :)
    And last but not least GABBY!!Very good advice right there, keep writing like you do, because I love reading it. I’ll tell my Internet friends about you :)

    PS: Sorry if it’s a shup-up-it-is-too-long comment. Btw this is my blog

  • sneakybacon May 21st, 2014 7:10 AM

    hey olivia,
    i’m 20 and have been in a sexual relationship for over 3 years now and it was literally only last week that i figured out how to make myself come with just my hands, so i really wouldn’t worry :)
    what i’d recommend in the meantime is using a vibrator (or even an electric toothbrush with a unused head on). the extra stimulation is often what some women need to come, especially when you’re figuring it out.
    also what i found helpful was watching something arousing, it took me ages to realise not all porn is derogatory and violent, so its worth looking around on the internet for something you like.
    In regards to fingering hurting it may just be a lack of lubrication. it might be a good idea to buy some or spend more time becoming aroused through watching things or fantasising. if this doesn’t work maybe do follow the above advice and see a gynaecologist, but i wouldn’t let it worry you yet, i still don’t like fingering myself, and theres nothing wrong with that.
    I hope this helps and remember to just have fun, there is no right time or right way xxxxxxx

  • Crumpets May 21st, 2014 7:26 AM

    Good grief, Amy Rose, you are just wondrous. You manage to be so articulate in a non-wanker-y kind of way. (That’s a compliment.) Thank you for existing and writing all of this weird relevant information.
    (I kinda want to hear the empty bathtub story now.)

  • Kaetlebugg May 21st, 2014 10:59 AM

    I would also like to point out, for the last question, that sometimes when you are with another person your body does stuff you totally don’t expect, or your feelings are heightened in a way that you just don’t get with masturbation – like when I penetrate myself with my fingers, even when I’m wet, it doesn’t really feel like anything, but when my partner does it after a great deal of foreplay, it feels amazing.

  • Kathryn May 21st, 2014 6:36 PM

    “paypal me a high five” amy rose is a one-in-a-million gem and a tru delight

  • kendallkh May 22nd, 2014 10:23 PM

    olivia: what sneakybacon said! (“its worth looking around on the internet for something you like.” i was bummed for years that i couldn’t get myself off but finally i realized that for me, just plain touching does nothing. once i started figuring out what i was into and looking around on the internet for stuff that got me off, then i could totally get going and it was no problem. just take some time to figure out what’s right for you!

  • Estelle May 23rd, 2014 11:51 AM

    “a herb who wants to feel a thing”

  • lauraunicorns May 24th, 2014 12:52 AM

    Hi, Lily! I don’t mean to be weird or anything but I hardly ever hear of any other Rookies existing in Alabama (which SUCKS – there need to be more of us), so I just thought I’d say hello from the same state!

  • lilshiek May 26th, 2014 6:36 PM

    I have the same kind of problems as Cass and, personally, I feel that your answer is insensitive and lacks a lot of empathy. At least in my situation, it isn’t about wanting credit or expecting validation. When my friends copy me, despite the ridiculousness, it feels as if she is directly robbing me of my INDIVIDUALITY. I’ve had friends tell my own personal stories about my parents and make them about her own parents, I’ve even had a friend say that her eyes were green when they were clearly brown JUST BECAUSE my eyes are green. It can be incredibly discouraging to be copied, though it can be a form of flattery. When a friend takes your traits or style without giving credit–pretending like those traits are THEIR OWN that came from THEIR MIND when they didn’t…. that is when it really hurts.

    Your point is clearly valid… but the number one faux pas in giving someone advice is invalidating their own feelings…. and the others that relate.

  • icanthinkofanythingoriginal May 28th, 2014 8:32 PM

    How do you send in questions?