I’m new to hooking up and I don’t know what to do

Dear Guys,

Okay, I’m that girl who really doesn’t date guys. I mean I usally don’t even flirt with guys I like, I’ve always been like this and I don’t know why! So here’s my problem. There’s this guy who I really like, but he’s moving soon. I don’t want anything serious, just kinda like a fling. I’ve moved things really fast because I’m ready to be “spontaneous.” Here’s the part I’m confused about. How do I tell him that I’m not looking for something serious? I’m not really experienced at these hook-up things—this would be my first time—and I’m not for sure what to do. Like, I just really want to get with this guy, but I’m stuck on how to ask if he wants the same thing. This guy is pretty used to dating tons of girls and I don’t want to seem completely ignorant when it comes to hook-ups.


Dear Ciery,

Thanks for your question.

While we aren’t going to encourage you to hook up with this guy—mainly because hook ups in general aren’t the best way to go, and if he’s hooking up with lots of other girls it could pose a health risk to you— we will answer your question. First of all, since he’s moving soon, that automatically places whatever the two of you do into the “casual” category. What else could it be unless you were both ready to try a long distance relationship? You don’t mention your age, but we’re sensing you are younger, so being able to sustain that sort of long distant relationship is unlikely.

So per your question: How do you let him know you want to be with him? It won’t take much. A little flirting, a few subtle hints. If he’s interested, or attracted to you at all, that’s all it should take. Guys are pretty simple. And if a woman they are attracted to shows some sort of interest in dating or sex, it’s pretty much a done deal. Once again, we don’t want to encourage you to do something you’ll regret later, but it’s up to you.

Feel free to ask us a follow up question. And please let your friends know about us. Thanks!


ps. You might enjoy our  “Relationship Memoirs”  page, especially Charlotte Pescale’s “Rebecca, a memoir.” (Introduction) Read the entire first chapter. Enjoy!

Other questions to check out: 

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Dating older guys: Video

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8 Comments on I’m new to hooking up and I don’t know what to do

  1. I’ve started into a serious relationship with a guy who I just used to be FWB at the start of summer. I was a virgin when we started but during our first hookup he just assumed I wasn’t and I went with it after he stated “he didn’t want his first time to be with a virgin” now that we’re in an actual relationship though I just told him last Friday that I really was a virgin and he seemed super relieved and excited because he really wanted to be on the same level with me. During this conversation I also opened up that I’d be willing to try different things in bed to kinda explore since I trusted him more but asked him to give me some time and if it’d be okay to work at my pace. Like with blowjob’s; he’s wanted one since day 1 but I havn’t been ready to give one! I asked him if I could get more comfortable down there and not give him an all out blow job but kinda figure out what works best with me. I asked if this would be too much teasing and he said no he was up for it.

    So 2 days later we were in his car hooking up (the whole back was down) and not 2 seconds into it he’s telling me to turn around to go for a completely new position 69! Now never giving a blowjob before and after just telling him I wanted to get used to it first I didn’t agree I just wasn’t ready! He kept pushing the issue until he finally gave in and we had sex instead and I promised to try 69 when we hung out on Saturday (he made me promise and told me that if i broke it he’d be extremely upset with me). The sex after was really rough on his part and usually I like that but it felt like he was mad at me and getting back at me through sex. During sex I asked if he was upset after a couple really hard thrusts and he said he was. I felt degraded afterwards like he had just been using me but we pushed it aside and continued on.

    Later after having sex one more time and having him finish on top of me he asked if I wanted to go down there and “practice” maybe just lick him a couple times. I was up for it and ready to try and I did have fun and really was starting to warm up to the whole idea of giving a blowjob soon. I use teasing to hide when I’m insecure about things and jokingly asked what he wanted me to do, he immediately started bring up a full blown bj again after I had just said not tonight and he promised to wait and that this was only practice. I got off of him and he told me that he was frustrated and that i shouldn’t of done that if he wasn’t going to get anything out of it (wasnt me going down their in the first place getting something!!!) but he had told me that he was 100% good with just me playing when we started!?!?!

    Right now I feel like I cant compete with my boyfriend sexually even though we are both virgins! He wants so much in bed and so soon ! It had only been 2 days since I’d even agree to start to try new things and he’s already frustrated with “waiting”! Am I just moving to slow for my boyfriend ??? How can I get comfortable with things if its always all or nothing and he gets frustrated with an in-between I want to try! We’ve only been together for 2 months and i feel like i give him a lot!

    I’m on BC so the sex is no condoms, i let him finish on top of me, i give him handjobs, I just started phone sex, and i’m willing to try new things like anal!!! and i’ve really started to open up to him emotionally but he always states that I’m a “taker” and he’s the “giver” in the relationship. Am I really taking too much in this relationship? How can I move faster and satisfy my boyfriend in bed! Am I just too slow and inexperienced!!!

  2. @Alex…..To us it seems like you’re moving quite fast for someone new to the world of sex. And your boyfriend shouldn’t be pushing you to do things you’re not comfortable with yet, and then try to make you feel guilty if you’re not willing. That’s not cool, and you need to be firm with him about what you’re willing to do and what you’re not willing to do. The sex should also move at your pace not his. (Pace should always be determined by the person who’s the least comfortable. That’s common sense. And respectful.) We do understand his urges though. A guy new to sex is almost out of his mind, especially a young guy. In fact that’s about all he probably wants to do in your relationship which is why he’s saying he’s a giver and you’re a talker. Alex, you need to slow down. You shouldn’t be doing things that you’re not completely comfortable with just to make your boyfriend happy. And you especially shouldn’t be trying to please him so he’ll stick around. Yes, relationships are about compromises, and giving, and trying to make your partner happy, but not at the expense or detriment of your own personal needs and comfort zone. Rest assured Alex, you’re already trying more things than many people much more experienced than you. Intercourse and oral sex are pretty common in serious relationships, but anal sex is not something everyone tries, or wants to try. Please go at your own pace. And if your boyfriend keeps pushing you, maybe you need to find yourself a new boyfriend. Good luck. Feel free to ask us a follow up question anytime. ps. Please let your friends know about us. Thanks! (And consider a small donation to THE GUYS.)

  3. Hey guys, I have a dilemma.  I’ve “hanging out” with this guy I met at a bar a few weeks ago.  Its been fun and we’ve been texting a lot.  I’ve seen him about 5-6 times and we have made out and tops have come off, but no sex so far.  I don’t know whether what we’re doing is causal or if he wants more.  Im not saying that I want to be with him the rest of my life or even a year, I just want to know that he’s going to stick around after I have sex with him.  The times we hang out has consisted of meeting places (theaters or coffee houses) and then going to his or my house to hang out.  We’ve made out 3 of the times we’ve hung out.  The last time I hung out with him, he wanted to go further, but I moved his hand.  After a while of making out, he kinda stopped me and we ended up cuddling for an hour before I left. We’ve still been talking, but he doesnt text me as much, but I still think its a lot for an average college guy.   How do I know he doesnt just want sex?

  4. @Analee…..You don’t. We don’t. However, let’s hash this out with some questions. How often do you talk? Does he initiate communication? Does he ask you out on proper dates? Does he pay? Does he act like a gentleman? Does he ask you any questions about yourself, or volunteer personal info about himself? Also, are you older than him? Meaning, is he in college and are you out in the working world? We need a little more info. However, at this moment, this seems like something casual and fun for him. Which would also tell us he’s trying to do this with other girls as well? (We’re not blaming him, just sayin’) So that would lead us to the conclusion that, even if he doesn’t dump you after the first time you have sex, it could go that way easily enough. Our suggestion: Be honest with yourself. It sounds to us like you kind of like this guy. If you want something more than just sex with him, we’d proceed with caution. Your thoughts? Give us some more info and we’ll see if we can provide some more insights.

  5. Well, we’re both in college. He has paid a few times, but we go to a lot of free events as well. We used to text all day, but he hasn’t texted me in a day. I always wait for him to contact me first. He acts like a gentleman, I had to initiate the times we did do anything. We talk about all sorts of things, from family to school, to his past. We aren’t very in depth with our conversations though. We just talk about our likes/dislikes and random information about ourselves and he usually tells me things without me asking him. I do like this guy, but I’m very scared of being taken advantage of. I’m also new to the dating game, I’ve only had one boyfriend.

  6. @Analee….Thanks for filling us in. We understand your hesitation, and we wish we could give you a definitive answer. The thing is, outcomes are rarely guaranteed in this life, but without taking any risks a person rarely gets what they want. There’s nothing wrong with proceeding with caution here; you should definitely keep your eyes open as you move forward. And trust your gut. But if you really like this guy, what choice do you have? You can either blow him off, or keep seeing him. Now just to confuse you more, here’s a little background on college guys. Many college guys aren’t looking for long-term commitments; and many feel that college is the perfect opportunity to meet AND sleep with lots of different women. They almost don’t see it as taking advantage of women; they almost see it as a privilege. Maybe privilege is too strong a word. But that’s the mindset of many college guys. Not ALL college guys, but many. Guys also take longer to mature than women. So part of that attitude is the way their brains are wired. Not an excuse, a fact. Does this help a little? Or are you more confused now? Ask as many follow up questions as you’d like. And keep us posted as this progresses, or what you decide to do. ps. Please let your friends know about us. Share our site on Facebook, Twitter, Pinterest, or wherever. We appreciate it. Thanks!

  7. I have this guy in my class whom I really really like. I tried for the past few months to get him to like me and go out. I asked him out once to go dancing with me over thanksgiving break. He said he would if he was staying in town but was going back home to Idaho. I know that was months ago. So when he came back. We talked and talked about school stuff. He never did ask me out and I never did ask him out explicitly again till last month. I asked him out on a Monday right before class. He clarified it would be a date before finally saying yes. So we set something up for Friday. Then on Wednesday, he told me that he would prefer not to since we are in the same class and he didn’t want things to be weird at school. He also mentioned that he wouldn’t go out with me because I’m married (technically been separated for several months but just haven’t divorced yet). so I said I understood although I was very disappointed. Not sure how to handle it with him now. I want to talk to him but feel kind of rejected. He ignores me at school even when I pass by him and say ‘hi’ but when the class went out on a picnic last weekend, he hung around me a lot. I caught him staring at me multiple times. He tried to show off at the pool every time I was there and left about a minute after I left the picnic even though all his friends were still there. Not sure why he did that. What do guys think after a girl asks them out and they say NO???? Is he doing it for attention? or because he still likes me but the situation makes it difficult to date? I know he has expressed feelings that he’s not looking for a serious relationship and I had told him that I was perfectly fine with that. Do guys like it when girls asks them out? is it a bad thing? or a good thing to do? if a guy thinks that he’s got a girl, do they not work at trying to get her anymore?? do they just give up? he has been posting all kinds of love songs on fb since I asked him out the first time which is unusual for him. And the fact that he made sure it was a date before saying yes, tells me he really likes me but don’t know how to act around him anymore. help!

  8. @Tammy…….The ball is in his court. Do not ask him out anymore. You’re making it way too easy on him. If he’s interested he knows where to find you. We just think he’s making excuses because he’s not that interested. Why? That’s not clear. It could be one of four things: 1. He has a girlfriend. 2. He’s not attracted to you. 3. He’s not comfortable with the fact you’re still married. 4. He doesn’t want to date an older woman. With kids perhaps? Let him do the work from now on.

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