Working It Out When Hooking Up Isn't Working


I'm 16. I've gone through 8 sexual partners in the last year. And 5 of them only in these past 3 months. I've only had one boyfriend in my life. I cheated on him. Twice.

I feel like I'm easy, maybe I am. I will tell myself that I won't have sex with a guy, and then I end up doing it anyways. In that moment I truly do want nothing more than to get it on. I am juggling two 'sex buddies' one of whom is a friend and the other is more of a stranger I sleep with. I suppose it wouldn't be such a bad thing except I only get sex when they want it. Frankly I'm a little fed up with this routine. I get horny too, but apparently that doesn't count. I enjoy sex, and I'm not afraid to say that. I can achieve an orgasm almost every time I have sex. But as soon as were finished I feel like shit. I don't really know why this is. I have inquired that maybe I use sex as a tool to make myself feel wanted and cared for. Or that I'm guilty to have maybe abused sex. Or simply that I am fucking... and not making love. I don't know what to do or what this is about. I don't know if you can console me, but any efforts and advice would be appreciated.

I want to first make a few things clear about any judgments you may be making about yourself or might assume will be made in my answer to you.

I don't like terms like "easy" when they carry derogatory judgments, for the same reason I don't like terms like "prude" used or internalized that way. If any of us feels personally empowered by, say, self-identifying as easy, a slut⁠ , a prude or any number of other words we might use to broadly classify sexual⁠ behavior, I'm down. I don't think that anyone else has the right to tell someone how to identify themselves or what words are or are not okay to do that with. But if you're applying those words to yourself and they make you feel bad, I'd ditch them. Making yourself feel bad on purpose is never helpful.

I don't think there is a "right" number of partners or that we can determine how many is too few or too many just by number or our age. What has been my right number of partners in my life, or your right number in yours, may be totally wrong for someone else. Often, people's ideas on what is too few, enough or too many are very subjective and often based in things like gender⁠ stereotypes or other character or value judgments that aren't sound when applied to others. I think what's important to look at is if we are feeling good about the sex⁠ and partnerships we're having, including if we're happy or not with how many of them we are choosing to have or have chosen to have. If one person feels best about two partners in their lives and another feels best about 50, I don't think either of those people are someone greater or lesser than the other; we're all different in that respect just like we're all different in how many friendships we have.

What "fucking" and "making love" means varies a lot. Some people use those terms interchangeably. Some people only use one. Some people use neither (especially those of us for whom the phrase "making love" conjures up very un-sexy memories of parents with waterbeds, cranked-up 8-tracks of Air Supply and too much cherry⁠ incense). In my experience in working in sexuality and being a person with a sex life, I think trying to fit all the different kinds of sexual experiences any of us can have into only those two terms isn't workable: sex is so much more diverse than that. I'm also not of the mind that sex for the sake of sex and sex that's about expressing romantic⁠ or other kinds of love are necessarily exclusive⁠ of one another or that one "kind" of sex is unilaterally -- rather than situationally -- better or more acceptable than another.

I want you to be able to read the rest of what I have to say while feeling good about yourself. I understand that you may have made some judgment calls that either weren't okay, or which haven't been in alignment with what you may really want and need, but that doesn't mean there is anything bad about you or that you are in any way deficient. Most likely all that means is that you're human like the rest of us and have potentially made some mistakes or missteps on the road to figuring out⁠ what's right for you, choices that have likely been part of figuring all of this out. Anyone who tells you that we don't all make mistakes most likely has not yet experienced much of life or is just not being truthful.

That all said, it's clear you're not very happy with your sex life right now. You say you aren't feeling good about your sexual experiences after-the-fact. You express feeling like your motivations for having sex with people might not be so great. You seem to be expressing that the sexual relationship⁠ you do have right now are more on your sex partners terms than on your terms, or based on mutual agreements and desires. You seem to be saying that even when you plan not to have sex, you end up having sex, despite your initial feelings.

As well, you say you cheated on a boyfriend. I don't know what your agreements with that boyfriend were, how they were made or if that was a relationship you were happy being in. It's obviously one thing if it was an unhealthy or unhappy relationship, or if you made an agreement to be exclusive when you didn't want to, but it's something else if it was a set of agreements you made -- being exclusive -- and made wanting to honor and a relationship you wanted to pursue and sustain. You also express what sounds like a potential issue with impulse control when it comes to sex.

It's clear you're feeling pretty crappy right now on the whole. Obviously, there's a bunch here that hasn't been right for you and that you're not feeling good about.

Ultimately, I think the first thing you have to ask yourself also happens to be something that can be the hardest to answer: What do you really want?

What are you looking for in your hookups? If you are, as you say, just wanting to get it on and are able to do that, is the problem about the dynamics of those partnerships not being quite right, or is it about you perhaps not really wanting that after all?

If in the sexual partnerships you're choosing, sex is only or mostly on someone else's terms, or only when someone else initiates, without any mutuality of response when you do, that's something you can change by seeking out partnerships where that's not the dynamic, and leaving those where it is. It may be that you need to choose your partners more carefully, perhaps spending more time getting to know them gradually before the relationship becomes sexual: you may need to be making sure who you're choosing has a good idea about what kind of dynamics you want before you get into bed with them. Before anything gets sexual, are you having any kind of conversations with potential partners about what you're looking for in a sexual experience or ongoing relationship? If not, you probably want to start doing that. You can absolutely tell potential sexual partners things like that you need to be able to initiate too and that you want a sexual exchange where you feel just as good after as you do during.

If that kind of conversation feels way ahead of where you or they are at, it may be that even though you feel the desire⁠ to be sexual, you might need some more time before you're at the point in your life and your own personal development where you can really cultivate good sexual partnerships and experiences. Just wanting to have sex doesn't make us ready for all it entails or make sex with any given person right for us at a given time. It also doesn't mean that any willing partner⁠ is the right partner.

When you find yourself feeling yucky afterwards, are you talking with your partners about that? You say one of your current sexual partners is a friend: we can talk to our friends about our feelings, that's one reason why they're friends. If you don't feel able to voice these feelings, but are having them, that suggests another adjustment you may need to make in partnerships. Why not choose partners you can be honest with and talk to, who do listen well when you do, being just as intimate with your feelings as you're being physically? Even casual partners, in my book, should be people we feel we can talk to and be honest with, especially if we're having a hard time. If these aren't partners you don't feel able to talk to about this stuff, but it's happening with them, or they're not responding to those talks with care, I'm perplexed about why you're not walking away from the relationships rather than continuing them when they're not working for you. If you feel obligated in any way to keep coming back to something that isn't working for you, that doesn't sound casual, like mellow "sex buddy" dynamics, to me at all. One of the benefits of casual sex, after all, is that we're able to easily walk away from it.

If you feel like it's not about specific partners or partnerships, or about how you're managing them, then you'll want to look more at yourself and at how you're coming to sex with others in general. For instance, not just in the moment, but overall, is "nothing more than getting it on," what you really want on the whole, not just in the moment? Are you even getting that in the moment if it's only on someone else's terms?

One tricky bit, especially for women, are strong, sexist messages out there that say women don't really like sex or casual sex, it's just something we do or accept when what we really want is love or acceptance. The thing is, there are many women's real lived experiences that make clear that isn't at all true for all women. At the same time, there are also real, lived experiences where women have found that to be true for them. But with such strong cultural messages, it can be tough to figure out what's truly true for you. I suggest consulting your guts. If you have a gut feeling that you have been, as you say, abusing sex in some way, or having sex when what you want is love or a more overall kind of care, I'd listen and respond to that feeling. It certainly is a possibility, especially if your intuition -- rather than someone else's judgments -- is giving you those cues. You being unhappy is another strong cue that how you've been doing things isn't working, potentially because what you've been seeking out or accepting isn't what you really want.

It can be hard to choose partners or relationships well if we're in denial about our own motives. If you are trying to seek out sex to fill your "wanted and cared for" box, I'm not surprised that's leaving you disappointed. It's not that sex can't be a part of that, it certainly can, but it's a lot to expect of sex to expect it to take care of the whole of those needs, kind of like it's be a lot to expect of one dinner if we expected it to take care of all of what we need to be eating in a week.

Sex is also more likely to play a part in getting those needs met when the relationships we're having sex in address those needs in other ways, too. If you're choosing partners who you know or suspect really don't care for you at all, and who don't give you any kind of care outside sex, it's probably pretty obvious those needs aren't going to get met with those folks.

Have you explored either other ways to feel wanted and cared for outside of sex or sexual relationships? For example, what are your friendships like? Are you investing as much time in cultivating and growing friendships, spending time with friends, as you are with sexual partnerships? If not, that's one thing you can work on adjusting. How about making sure that you're doing other things in your life that are part of getting those needs met and meeting them for others? Volunteer work, for instance, can be an excellent way to feel valued and needed. How do you think your self-esteem is? Do you hold yourself in high esteem or not? If you don't, that's something else to do some work on, and sexually, something that supports that is doing your best to choose sexual relationships or situations where you feel respected and like who you are, and what you want and need, is privileged just as much as who someone else is and what they want.

When you were with that boyfriend, was that a relationship where you felt cared for? Was it something that made you feel good? If it was, but you had sex outside your agreement with others, and/or were dishonest about that, chances are good it's because you were scared of something or trying to self-sabotage the relationship. Sometimes even when we want to be cared for and loved, it can feel scary to start to actually get that and can feel easier to just bolt or go swimming in shallower ponds, especially if we have had any hard issues with our family or other intimate relationships. Sometimes being with people where we know or feel they won't care from the start can feel safer than being with people who we know do care for us because the emotional stakes are higher. Per my own ethics, I think if and when we are having sex to try and avoid or run away from something then that is an abuse⁠ of sex, and also is not likely to nurture a sex life, or a self-image, we feel good about.

You make clear you've only had one boyfriend in your life. That's not unusual for your age, and I'm not on board with the idea that sex is any more or less acceptable within or without romantic relationships. But when you say that, do you mean you would prefer a romantic relationship to hookups? If so, then I'd suggest you seek out what you want and hold out for what you want, rather than accepting anything you don't (if that's what you're doing) or just taking what you feel is available to you.

I also hear you saying you enjoy sex and aren't afraid to say that, but you say you're in sexual partnerships where your own sexual desire isn't being addressed. That leads me to believe that you probably aren't really being so bold, after all, in what you say about your sexual needs and desires. If you are saying what you want and need and the other people are either blowing that off or just don't have the same needs, then those are reasons to ditch those sexual partnerships, because they clearly aren't working out or aren't with people that are a good match for you. If you're not speaking up for yourself and what you want and need, that indicates that either these people aren't sexual partners you earnestly feel comfortable with -- another good reason not to be in sexual partnerships with them until you do feel that level of comfort -- or that you don't yet feel able to assert yourself past what they want from you. If the latter is the case, then you may need to work more on your own assertiveness before any kind of sexual partnership really works well for you.

By the way, I know that it can feel like if you're able to have casual sexual partnerships then you must already be very assertive⁠ , but that can actually be illusory. It's not assertive, for example, to just be responding to other people's needs and wants from you without speaking up for your own wants and needs and insisting they're treated as important.

In my book, this is the difference between "putting out" -- which is about supplying someone else's demand -- and having sexual partnerships or experiences in which everyone involved is an active partner, where sex is about people sharing something, even in casual contexts, and where someone is treating themselves and being treated as a whole person, not just a receptacle or supplier for someone else, if you follow me. I don't think that if what you want is casual sex that means you can't still have relationships with those partners which have all of those beneficial elements. However, I do think a lot of people come to casual sex, especially when it's new or they're without a lot of emotional maturity, with the idea that they don't have to deal with anyone else's feelings or desires. I'd posit that when someone wants that, they don't want any kind of sexual partnerships at all, even a casual one: those motivations are the kind where masturbation⁠ is what's most suitable. If none of us wants to really deal with someone, it doesn't make much sense to be having sex with them.

I know that none of this is easy to figure out, especially if you're feeling overwhelmed. So, sometimes when we're stuck in a lousy pattern, we've got to step outside of that to get a clear look at it. I think if you stay in these relationships and scenarios now, and don't take some time away from them, you're probably going to stay stuck.

The number of partners you have in the short amount of time you have had them tells me that you haven't taken much time between partners. What taking time can give us is needed perspective: time to think about what was good and what wasn't outside relationships so that we can consider any relationships or partnerships afterwards with what we learned from the past ones. This is one of the ways we figure out what we want and what we don't. It's way harder to try and process our feelings from one experience or relationship when we're in the thick of another. Taking time between can also can leave you feeling a lot better adjusted and appearing a lot better grounded to others: if other people are reading you as a hot mess, then you're likely going to draw the kind of people to you who are either a mess themselves or are looking for someone else who is so that they don't have to step it up in any way. As well, with two ongoing booty calls and that many partners in that short time, you probably don't have a lot of time for anything else in your life, so it's going to be hard to assure your life is well-rounded. We all need more in our lives than sex to feel good about ourselves and to get our needs met.

How about giving yourself a few weeks -- longer if you find you need to -- without partnered sex? Stepping away from casual relationships for a while should be no big whoop, since no one should have any expectations of anything continuing. You can tend to your own sexual desires with masturbation in the meantime and see how you feel without these partners. You can make lots of time for yourself to think more deeply about all of this; to be able to see it a little more objectively outside the whirlwind. You can perhaps also be able to put your finger on what, if anything, you feel like you're missing when you're not in any of them, and also what you're getting that's positive by NOT being in these situations. You can take time to talk to a friend, a parent, a sibling or some other person whose opinion you value and who you know cares for you to see what they think.

Maybe you'll find out that it's just that these particular partners haven't been a good fit for you and this is a matter of being more selective about partners, taking more time to choose them more carefully, and with a better handle on what you really need, needs you need to voice more clearly and boldly, nixing partners who aren't going to be able to meet them. Maybe you'll find out that none of this, no matter who the other person is, is actually what you want at all, and you need to take some more time off to figure out exactly what that is, or to tend to other needs of yours that sex with people just isn't meeting (and may be keeping you away from). If you've been looking for something in places you're unlikely to find it, time off can help you find out what that is and start to identify better places to seek it out.

If you don't choose to take that time away, and have sex again and feel like this, I have another suggestion. The next time you find yourself feeling cruddy after sex, quickly pull out a pen and paper (I know that's likely to be a bit socially awkward if you're not being emotionally open in these relationships, so sneak into the bathroom to do it if you must) and write down what you're feeling very freely. leading with your heart. Don't worry about it making any sense or being constructed well, just write in a stream-of-consciousness way. Write out what you feel like, how you feel about yourself, what you wanted but didn't get, what feels like it's missing, what you wish were different in that moment or in the moments that led up to it. Journaling like that can be a great way to access inner feelings that can be tough to get at otherwise. Later on, take a good look at what you wrote. See if you can't find some cues about what you really want and need, then consider what different choices you can make to get that. Value your own words and feelings: I hear you suggesting others aren't treating them like they matter, but you most certainly can yourself. If you're not valuing and honoring your own feelings, it's going to be mighty tough for others to.

It also sounds like you might benefit from some counseling. Counseling is really helpful when we're feeling "stuck" at any point of our lives; when we know we're not happy and aren't getting what we need, but are feeling lost about why or can't figure out how to get there. A good counselor is trained to help a person get to the core issues in those kinds of situations and then help you figure out what steps to take next. You also express that what you want in a given moment possibly isn't what you want in general, or find that you want afterwards. That may indicate you need some extra help with making sound judgments for yourself and with managing impulse control: a counselor can help with those things, too.

I know that when counseling involves talking about sex and disclosing sexual activity and you're young, that can feel particularly precarious, but you can screen counselors before you sign on with them to get a sense of if they can talk to you about sex without judgment. A judgmental counselor isn't going to be of any help here. Luckily, plenty of counselors who work with young people know that and won't judge: their interest will be in helping you feel better and be living a life you like better, not about making you fit their ideas of what is "proper" behavior.

Lastly, I want to check in on your sexual health. Having multiple partners does mean our risks of sexually transmitted infections⁠ are increased. I want to make sure you know, in case you don't already, that with the amount of sexual partnership you have been having it is critically important to your health that you are using latex barriers (like condoms) for any and all oral, vaginal and/or anal sex⁠ and that you are also getting tested more frequently for sexually transmitted infections than someone in longer-term or singular relationships would need to be. With more than one ongoing partner at a time, I'd advise testing at least twice a year, more often than that if you're not using latex barriers every single time, from start to finish. I'd also strongly encourage you to choose partners who are getting their own testing done. Most STIs are not the end of the world, but identifying any early is important for your health, as is trying to prevent them. After all, if you're feeling shitty already, an infection⁠ is not going to make you feel any better, okay? If you're not up-to-date with your STI⁠ testing, please go and get current with that to take care of yourself. As well, since your profile says you're female, and you're sleeping with guys, hopefully you also know there are pregnancy⁠ risks here you'll want to manage by always using reliable birth control⁠ properly, be that condoms alone or using another method with condoms.

I'm going to leave you with some links. One I think would be good for you to go through carefully is the Readiness Checklist. It may feel rudimentary in some ways since you feel like a very sexual person and like sex a lot in some ways, but just remember that neither of those things alone ever means all of us are in the right space for sexual partnership at a given time. It sounds to me like there may be some of the emotional and interpersonal bits on that list missing in your own readiness (or even just your wantedness) that you might need to work on before continuing with sexual partnerships. People of all ages who love having sex and feel very sexual still have times when we know we're just not in the best place to be sexual with others, and would take care of ourselves best by having some downtime to regroup and recenter.

I support you in wanting whatever it is that you want. If what you want are more casual sexual hookups or experiences, if what you want is this many partners or that few, I'm good with that, so long as what you're seeking out and participating in really is what you want, is something you do with care for others and yourself and that leaves you feeling good before, during and after most of the time. I'm not of the mind that casual sex has to be something that is or feels empty, but if it does or doesn't have that impact has a lot to do with the way we manage it, the choices we make around it, and being sure that at any given time, it -- and who we're sleeping with -- really is best for us and is wanted, rather than being something we do because we don't feel worthy of other options or because we're afraid of something, whether that's about a fear of being alone, being unwanted, saying no (or hearing no) or getting close enough to someone to have them see who we really are, not just who they (or we) might want us to be.

Similar articles and advice

  • Heather Corinna

If you had a partner before him for oral, vaginal or anal sex, that could be who you got it from and your current partner managed not to contract it from you (now or yet), or contracted it so recently that he isn't testing positive yet. Or, your current partner's test wasn't accurate, or he said he…