Haven't dated since Highschool... help!
May 2, 2009 6:24 PM   Subscribe

I'm in my mid 20's, and I haven't dated since high school. How do I do this right? (uh, NSFW)

I haven't dated since high school. My high school relationships were pretty decent, I had 3 that lasted almost a year, plus the usual fooling around in between. But I was a pretty good girl back then.

Since then, however, I haven't been in a relationship. Haven't met a guy at a bar, haven't even kissed someone, or held a man's hand. Why? Well, I went to a private University, and since then I've traveled/lived internationally a lot, and the few expats in those places are usually much, much older than I. And also, I'm just not the kind of girl who's into anonymous one night stands, or being with a guy "just because". I value relationships, so I'll wait until a decent guy comes along.

Fast forward to now. (my friends want to set me up with a guy I met last week, who I clicked really well with, but this is also a general question) How do I date like an adult? I'm a pretty well balanced, intelligent, mature individual. It's just that my most recent relationship started with "Will you go out with me?", ended with "My mom says we have to break up", and was filled with lots of notes passed in class, and hiding from parents, in between. Ridiculous.

And... about sex. My last tromps? With a barely-pubescent highschool boy on prom night, we had no idea what the hell we were doing, and no, we didn't have sex. I'm a virgin.

Any, any advice at all is appreciated, and I feel like my questions might not even have specific answers, but here's a few to get you started:

-How do typical adult relationships happen? ("typical" is probably the wrong word, though, I know there isn't one)

-I feel like, if I do begin a relationship, I may at first be either highly overwhelmed, or incredibly "giddy"... not because I'm not ready, but because it's been so long since I've been with someone. Excitement is good, but I don't want to push a guy away. How do I keep my emotions/expectations realistic?

-sex: Aside from the million obvious ways, how are sexual encounters with a 25 or 30 year old man different than those with a 15 year old boy? I'm a (technical) virgin, and plan on staying that way till marriage, ( if a guy doesn't understand that, he's not the kind I want to be with anyways), but I'm fully open to the rest of the options. I just don't know what to expect in bed or on the way to bed, and what he expects from me (communication is key, though, I know).

I'll leave this for now. I feel as though I may be coming across a little more "overthinker" than I really am, but this is ASKmifi, so I figured I'd just lay it all out there. Communication in a relationship is number one. I know that. And I'm not rushing into things; life and love will happen as they may.

So, mefites. Advice? Suggestions? Anecdotes? THANK YOU, in advance!
posted by anonymous to Human Relations (16 answers total) 20 users marked this as a favorite

You're psyching yourself out before you're even getting started. I think your maturity level will guide you normally through the whole dating process. And even people who have had uncountable relationships always get giddy/excited when they meet someone new and experience life with them.

So, I guess my only advice is not to overwhelm the guy with texts/calls. Keep it light and fun, things will progress naturally. I was in the same boat as you not many years ago, thought too much about things and just went with the flow. You already have your mind made up on sex. Let him know about what your stance is then as things progress I would think that it probably wouldn't be much different than your high school days, just not as clumsy. Again go with the flow, you'll know when things are getting out of hand for your tastes and just reel him back in saying I'm not ready for this slow down, you know the drill.
posted by mi6op at 6:34 PM on May 2, 2009

Internet dating - it really works, there are people out there just like you waiting to meet you just like you are waiting to meet them. Date a bunch of people. Lunch dates if you are nervous. Eventually you will meet someone that you want to go on a few more dates with.
posted by caddis at 6:47 PM on May 2, 2009

Also, you seem to be too focused on a relationship when you should be focused on just dating and having some fun. A relationship will just happen naturally if you date enough different people. If you try too hard on the relationship front it just won't work. You will seem off to potential relationship partners.
posted by caddis at 6:52 PM on May 2, 2009 [2 favorites]

When you're meeting new people for any reason, you want to put your best foot forward, but when looking for a relationship, don't let this get in the way of being yourself. There are a lot of guys out there who will like you for who you genuinely are and for how your genuinely behave. Don't play games with things like waiting to call, initiating contact, or escalating the relationship.

Be yourself and you'll attract guys who like you. Most people I know who are looking for relationships spend a lot of 2-3 week courtships trying to do everything right and impress the hell out of the other party before discovering that they can't be their true selves with that person.

Good luck!
posted by chudmonkey at 7:01 PM on May 2, 2009 [1 favorite]

How do I date like an adult?

You assume to much. There is no "way" to date. You're a human being, right? You're an adult, right? If you answer yes to both of those, then you're well on your way to having perfectly normal, bland, unexciting dates just like everyone else.

I'm a virgin.

For anyone who doesn't attach magical significance to penetration, this is a meaningless designation.

Do you masturbate? If so you know your own body and what you like. The trick is transmitting that to your partner.

How do typical adult relationships happen?

First, physical attraction, followed by emotional connections. You see someone you think is cute, you talk to them and realize they are either a doorknob or interesting. From there you're just a few outings away from a relationship.

how are sexual encounters with a 25 or 30 year old man different than those with a 15 year old boy?

Well, hate to burst your bubble, but almost ALL men you date in this age range are going to expect sex at some point unless you live in a country where women are stoned for seeking education. Toward your later 20s, people who aren't married, are generally seeking partners who they are not just compatible with emotionally, but also physically.

I'm a (technical) virgin, and plan on staying that way till marriage, ( if a guy doesn't understand that, he's not the kind I want to be with anyways)

Speaking as the "kind" of guy who you wouldn't go out with I can say that there are penny loafer wearing, virginal guys out there, or so I've heard, who will completely be excited that your flower has yet to be "technically" plucked. Generally I find these sorts to be a little "off" and creepy (especially if they have made it to their late 20s or early 30s unmarried,) but I'm deeply biased about sex and virginity.

Here's the problem: the vast majority of guys out there are going to want to date someone who puts out. You're not that person. So you need to either a.) develop a solid quiver of "hints" to make it clear to most guys that you don't do the nasty, or b.) you need to come right out and say it on the first day.

And I'm not rushing into things; life and love will happen as they may.

On the contrary, given your specific self-imposed chastity, I think you should be as up front as possible with the men you date.

As a woman who sounds like she is willing to do "anything but that" all the way up to hopping in bed, you risk coming off as a tease. That's a harsh assessment, I know, but it's the reality. And no one likes a tease. You don't understand how guys set themselves up for a sleep-over. We actually clean our apartments, make sure we have condoms, change our sheets, masturbate like 20 times before just to make sure everything is working, and so on... to get that far into it and to be told, "oh, by the way, I don't put out," is cruel.

Do the VAST MAJORITY of guys who you're going to date a favor: cut to the chase and tell them the it ain't going to happen. It'll save everyone a lot of grief (not to mention time and money.)
posted by wfrgms at 7:01 PM on May 2, 2009 [17 favorites]

There are a dozen askmes like this in the archive (I should know - I wrote one!) so I would suggest reading the answers to those, as well. As personal and problematic as your situation seems to you, it's actually pretty common, and the advice I've seen given tends to be pretty generalizable.

That said:

How do typical adult relationships happen?

There's no "typical" way that adult relationships happen, although there are certain conventions that have taken the place of note-passing and getting your best friend to call his best friend to ask him out (yes, I did this). "Would you like to go get coffee sometime?" is a pretty good phrase to practice, and you'll want to make sure you understand the intricacies of body language, but other than that - a relationship can start from anywhere. A friend of a friend you meet and have chemistry with. A guy from a party. A guy you meet volunteering. Etc.

I think the biggest difference is that when you're young and everyone knows everyone and who's dating who and who dumped who is that there's a heightened fear of rejection. If you're going to have to see the guy who rejected you every day in calculus, why take the risk? For me, getting over those worries has been the biggest part of becoming an "adult" dater. Because as compelling as they are, they're no longer practical. If the guy you like wants to date someone else? Guess what - you never have to see him again. So man/woman up and ask him out.

Getting over that fear can be especially hard if you feel like an inexperienced freakazoid. But you're not, and learning how to put yourself on the line like that is one of the single best things you can do for yourself.

Aside from the million obvious ways, how are sexual encounters with a 25 or 30 year old man different than those with a 15 year old boy?

I never had a sexual encounter with a 15 year old boy (and never will, I certainly hope) but I was a late bloomer and the first time I had sex was with a guy who had been around the block a few times (and he'd been going around the block for years). He knew what he was doing, which I found incredibly relieving.

Telling him that I was a virgin - and that he was my first real relationship - was very tough, but he was kind of perfect about it - he told me that it didn't bother him at all, that he was touched by the fact that I trusted him enough both to confide in him and explore with him, and that he would go exactly at whatever speed I was comfortable with. Not everyone is this awesome, unfortunately, but the good ones are, and it's a reaction you have a right to expect.

I think the key is really to be comfortable with yourself - not embarrassed or ashamed of your virginity (and it's nothing to be ashamed of!) - familiar with your own body (what turns you on? what gets you off?) - and to recognize that any kind of sex, even between the two most experienced people on the planet, can still be awkward, silly, messy and surprising. If you've got a healthy attitude - and a good partner - then you'll be fine, I promise.

Finally/on preview - I've never had to navigate the waiting-til-marriage issue, so I'll leave that to more capable MeFites. But I wanted to provide a counterpoint to wfrgms - there are plenty of fun, exciting, non-penetrative ways to get off/get a guy off which it sounds like you are comfortable with/maybe even experienced with. Yes, communication is really important and no, not everyone will be compatible with you in this way - but guys like that do exist and just because you couldn't date someone like wfrgms doesn't mean you shouldn't hold out for someone you can date.
posted by shaun uh at 7:15 PM on May 2, 2009 [1 favorite]

Relax. Go on dates. Decide whether you like people who like you. You can make decisions about what to do in specific situations as they arise, but stressing yourself out about the myriad ways a relationship can progress beforehand will just make you crazy.

Also, while I'm not going to go as far as wfrgms does, I will say that most men who are still single in your age bracket are likely to fall into one of two categories. They will either be no-sex-until-marriage types (often religious) who have a broader definition of sex than you seem to and will not consider "the rest of the options" acceptable behavior for single people, or they will not share your views about penetration and will eventually want to have intercourse with you before marriage. You have somewhat unusual views about sex, and you should probably be aware that most people you date will not share them, one way or the other.
posted by decathecting at 7:22 PM on May 2, 2009 [2 favorites]

I'm sure you've learned a lot about human relationships in the past ten years. Probably a lot of the same lessons other people learned through dating. That being said, there are certain thought processes one has to go through oneself. It's like the first time you do anything, you have to think it through. You're a couple years behind the cool kids, but that's ok, they don't have it all figured out yet either; everyone is at their own maturity level. Therefore my advice would actually be not to go with the flow, as mi6op suggests, but to reflect a little bit more than the experienced person, about dating, since you've got new neuro synapses to build. For example, you've asked this question. That's a good start. Continue to write your thoughts down. Beanplate the hell out your upcoming coffee date, or whatever it is. Learn all you can from it. Also, remember, your dating pool is guys who are Ok with "no sex til marriage." Those guys don't have much experience either. You'll catch up very quickly.
posted by metastability at 7:23 PM on May 2, 2009

You have somewhat unusual views about sex, and you should probably be aware that most people you date will not share them, one way or the other.

Actually, in a lot of evangelical and/or fundamentalist Christian communities, the de facto mores among teens and young adults are similar to the anonymous poster's--only penis-in-vagina sex "counts" as premarital sex, while oral sex, manual sex, dry sex (a/k/a humping or frottage), and even sometimes anal sex aren't considered to be "real" sex. (Here's an interesting book about the phenomenon--it's written by someone who is advocating for more thorough sexual abstinence in the service of Christianity, which is not my point of view, but the interviews and perspectives she relates in the book are fascinating.)

This is not my own point of view, and it is certainly not the de jure mores advanced by any religious or ethical tradition, but it is not at all uncommon in some subcultures.
posted by Sidhedevil at 7:36 PM on May 2, 2009

You have somewhat unusual views about sex

Actually, I'd say you have incredibly common views about sex (among high school and college-aged girls who haven't had a boyfriend yet). So there's that - you may find that you change your mind once you meet a guy you want to everything-but with.
The good news is that most people - even those who had relationships in school - don't go on "dates" per se until they're out in the world. Usually with college relationships you're friends first, then you make out, THEN you go on dates so "dating" where you meet a stranger for drinks to size each other up is new for most everyone your age. And it's scary for everyone! So don't think ugh this is nerve wracking because I'm so inexperienced - it's that way for everybody - but it's also really fun. I was your age the first time I Internet Dated and it was really exciting - I felt like a Grown Up Lady in a Movie! Or on a TV Show!
posted by moxiedoll at 7:43 PM on May 2, 2009

I think most adults want a sexual relationship, but I think the pool of guys who are willing to be in a relationship that involves sex but not necessarily vaginal intercourse is a lot bigger than wfrgms implies. I think it's also incredibly common that people think they won't want to have sex before marriage but change their minds after having adult relationships. So a lot of guys might think you will change your mind later, given your inexperience. If they don't take what you say at face value and are wrong about their prediction, then that's really their problem. But it means that even guys who want to have intercourse would date you for a few months.
posted by grouse at 7:57 PM on May 2, 2009

I know plenty of devout Catholics, Mormons, Muslims and evangelicals who are decidedly NOT creepy....and who are also virgins over the age or 25 because they're serious about the "wait til marriage" thing. It happens. Dating men within your own faith community will make it easier to find acceptance for not goin' all the way.

If you're not planning on holding out due to religious beliefs, though, be aware that views on premarital sex often, uh, change, among people as they become more sexually active.
posted by availablelight at 8:28 PM on May 2, 2009 [1 favorite]

if a guy doesn't understand that, he's not the kind I want to be with anyways

I actually think there are plenty of men who are kind, upstanding, and moral (and who certainly don't think of sex as something women are expected to "put out"), who would also respectfully question the distinction between intimate sexual activity and "technical" sex. People's attitudes change over time, and I think a lot of people who start out finding that distinction useful come to question whether it's really all that valid or meaningful, as well as change other attitudes about (especially female) sexuality.

I'm not trying to push any particular view on you (and of course, you obviously shouldn't date someone who doesn't support your right to make your own decisions). I'm just trying to say that there are other ways to see it all -- ones held by plenty of people who hold themselves to the highest moral standards -- and if you assume that yours is the only right way to see it and judge men who see it otherwise, you might miss out.

Anyway, it sounds like you're about to start something fun and exciting. Have fun!
posted by salvia at 10:49 PM on May 2, 2009 [4 favorites]

I'm a (technical) virgin, and plan on staying that way till marriage, ( if a guy doesn't understand that, he's not the kind I want to be with anyways)

You need to join a conservative church, preferably Christian, Mormon, or Muslim, or join a conservative internet dating website where this sort of thing is known to all participants. That is the only place where you will find a man willing to wait until marriage. If you're not up front about this peculiar stumbling block, you're going to waste your time and that of others. Good luck.
posted by Optimus Chyme at 10:27 AM on May 3, 2009

To be honest, I'm not sure I can provide good advice on the sexual aspect without understanding why you are committed to being a (technical) virgin and what exactly you have in mind as being a permissible alternative in bed or on the way to bed, as you put it. I agree with some others that the average, not particularly religious man will have certain expectations as to sexual relations, and you are cutting into the talent pool by ruling it out, but you make your own rules.

But putting that aspect aside, if I were you, I would totally ignore the fact that I'd not been dating since high school, and bluff your way through that (without inventing relationships or otherwise deceiving). Basically, nothing about dating is so well resolved, or so skillfully and universally well managed, that you should be intimidated by your lack of experience, or communicating that to your partners. I would grasp whatever opportunities I could find to build some experience, and not worry about not having had it before.
posted by Clyde Mnestra at 6:57 PM on May 3, 2009

Agree with Clyde Mnestra's prior comment. Even though you say you aren't as analytical as the post suggests, it is clearly important to you and worthy of thought. That said, I had a totally opposite experience in the details, but very similar in the sense of time passing and having to evaluate how to "reenter" dating life.

Practice Practice Practice!!!!! And read this book.

It's easy to put all of our eggs in one basket, believing in a true-love/soulmate, while the reality is often less shiny. I found that waiting and waiting and waiting for that ONE, meant I missed so many opportunities to love, be loved, grow, hurt, forgive, be happy, be crazy, make mistakes, learn and teach. There is no such thing as a perfect relationship but you must trust yourself, and I'd highly recommend allowing the less-than-ideal-I-know-he's-not-my-forever guys to enrich your skill set in the meantime. It's very easy nowadays as a modern woman to bury your nervousness/expectations in jobs, friends, shoes, parties, etc., believing if you are a well-rounded, great girl, your prince will still magically rescue you, and before you know it, you're the cat lady (did I just cut that from my profile???). Every relationship (romantic or otherwise) teaches us something about ourselves, and the more you practice, the "better" you get. Don't discount the wealth of relationship experience you've amassed on your travels and through life just because you weren't making out with all those silver-foxy expats.

Try to not get pressured into thinking this singular aspect of you is open-season for discussion. Yes, you will lose many guys along the way who won't want to wait, but it is undeniably true that if they care about you, it won't be the only factor, so discuss it within your comfort level. Again, practicing makes this massively more easy. Would you rather invest 5 whole days of your time, heart and energy on one guy you think is marriage-material, only to find out that when you drop the v-bomb he bounces, taking a little smidgen of your hope or confidence? Or spend 1 day each with 5 different people you're lukewarm about, maybe only like 2 as possibilities to go out with again, now down to 1 guy, who by this time has made it to a 3rd date, at which time you'll have an automatic boost of ease and esteem simply from having survived 5 first-dates and only spending 8 days of time!!! It sounds cold and calculating maybe, and I'm clearly filtering this through NY-sized dating pool ratios, but I swear it will exponentially increase your comfort to not let it all ride on one bet.

If it doesn't turn your stomach, you could also just "get it over with" anonymously or with someone trusted to clear virginity off the table. Alcohol is a revered age-old scapegoat if you need to later justify it. (this is only a partially serious suggestion not meant to offend)

Good luck and enjoy the journey.
posted by canijusa at 3:31 PM on May 6, 2009 [3 favorites]

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