casual hookup etiquette for the post-serially monogamous citizen
March 25, 2013 12:00 PM   Subscribe

After many years of monogamy followed by several years of celibacy (continually enforced by the fact that, out of raw fiscal necessity, I will continue to share a house and mortgage with my ex for the indefinite future), a chance encounter has left me with the opportunity to enjoy one (or, fingers crossed, more than one!) casual hookup(s) with a breathtakingly attractive near-stranger. Can you walk me through this process -- safety, guidelines, what to do/not do or say, etc. -- like a complete newbie?

I (early 30s woman) recently traveled out of town to have dinner and see a show; at dinner, I flirted with the bartender (early 20s man) because he was Just My Type, and I could not resist. I expected nothing, of course; IME it is always in a bartender's best interest to flirt with all customers, regardless of looks/gender, because tips! However, as the restaurant hours drew to a close, I was very surprised to hear the kindly barkeep ask if I wanted to grab a drink and then go back to his car to make out for a while. ("Uh, yeah!")
"A while" turned into a few rollicking, exceedingly enjoyable hours; we've since exchanged all relevant contact/personal information, maintained regular contact, and have now made tentative plans -- a week from today -- to meet at a random business traveler-type hotel in a commuter town midway between our cities, basically just because we both think it would be hot.
Current plan is to just head over there sometime in mid-afternoon, see if they have a room available, and see where the rest of the day/night takes us. (We are unlikely to stay overnight because I have to get up early for work the next day; I know we won't be penalized for using the room for only part of the day so long as we leave the key whenever we depart, so no worries there.)

I think he might think that I'm some kind of vivacious, uber-experienced vixen based on our interactions and conversations thus far, but the truth of the matter is that I HAVE NO IDEA WHAT TO DO. I was in a committed relationship for nearly a decade and had not had any sort of romantic interaction with any man, even a kiss on the cheek, in the 2.5 years since that relationship ended... until I met this one. However, my 20s were completely wild and his 20s seem to be proceeding in much the same way, so I feel like I can meet him where he's at without too much trouble.

Already established: Prospective hookup partner and I are already 100% on the same page in all routine and practical matters, fully engaged in both the practice of asking sexytimes-related questions without any hesitation or embarrassment and the participation in all X-rated activities with consistent and enthusiastic consent. While I've enjoyed his company immensely, we have a great deal in common, I think of him highly as a person (albeit one I barely know from Adam), and I would be totally down to 'date' him if we lived in the same city or either of us was interested in a monogamous relationship -- the bottom line is that this is either going to be a one-off casual hookup or the first in a series of casual hookups.

So! Having been out of the proverbial game for a very long time, and with nearly all of my friends having already been married/otherwise out of 'hookup culture' for many years, I have a few practical questions:

1. Do I get tested for STDs before we meet up, and/or tell him up front whether I have or have not done so? I haven't slept with anyone but my ex in half a dozen years, and haven't so much as kissed anyone at all in close to 3 years... but should I go get all fully checked out before this thing happens, just in case?
2. Do I ask him if he's done the same and, if he hasn't, request that he do so in advance of our encounter? He is currently actively engaged in several other purely sexual relationships, so I'm not sure what his testing status/policy is. I would have no problem asking or outright requesting, but is this even an acceptable thing for a near-stranger to ask in this situation? Or is it mostly "don't ask, don't tell, just use condoms and try not to stress too much"?
3. Aside from using barrier methods and common sense, is there anything else I need to worry about in terms of staying protected? (We will not be engaging in any particularly risky behavior.)
4. Are there any other rules of engagement when it comes to casual hookups? EX: What if I want to hook up again? I admit, I've not done anything remotely like this outside the context of having brief flings with touring rock musicians, who were always easy to deal with because they'd just leave in the morning to go to the next city, so I'm not sure what the repeat performance guidelines should be.
5. Anything else I should keep in mind? (Who should pay for the hotel? What should he/I plan on bringing, if anything? Once the ball is rolling, how do we keep it in motion?)

Anonymous answers can be addressed to

Thanks much, AskMe!
posted by electroshock blues to Human Relations (15 answers total) 5 users marked this as a favorite

1. It's never a bad idea to get tested even if it's just for peace of mind. You absolutely should come clean about whether you have or haven't, and give him the 411 in terms of status for testing/diseases/etc. It's a sign of respect for him (I mean, if don't respect the guy enough to give him honest information that would affect his health, you shouldn't be sleeping with him).

2. I wouldn't demand testing, I would just ask what's the what with him.

3. Aside from the barrier methods and safe sex, I would definitely just ask what's the what with his testing/STD statii.

4. If you find out, let me know.

5. I'd maybe offer to go halves on the hotel. The whole cost would be a big hit for him, I think; get that settled before you get into this, so if he's totally broke you aren't both caught short. As for what to bring - y'all each got your bodies, that should be plenty. Just pack extra condoms in case you want a second round, and maybe a change of clothes in case you stay over after all/something gets ripped/you just wanna change/whatever.

And have fun.
posted by EmpressCallipygos at 12:09 PM on March 25, 2013

Use a condom, don't fall in love. Bam. Done.
posted by fshgrl at 12:11 PM on March 25, 2013 [15 favorites]

Mod note: OP, could you provide a non-mailinator address via the contact form? Mailinator email can be read by anyone.
posted by jessamyn (staff) at 12:12 PM on March 25, 2013

1. if you want to get tested, get tested. though if he asks, and you haven't, then don't lie about it.

2. don't demand he get tested. use a condom. if this proceeds into a more-than-just-a-one-time-thing then at that point, you can ask him to get tested before you stop using barrier protection.

3. nah. condoms. i would tell someone where you're going and who you're meeting, though, so if you turn up dead, the police will have a lead. source: ALL THE LAW AND ORDERS.

4. there are no hard-and-fast rules on casual hookups. no if this, then thats. if you want to hook up again, text "what are you doing later?" - that's like secret code for bangarang time. if he's interested, he'll let you know. if he constantly blows you off, that's him not being interested in doing it again. on the flipside, if you're not interested in doing it again, don't feel pressured to.

5. bring a couple of bottles of water - i hate drinking hotel tap water, and sex makes you thirsty. as far as paying, offer to pay for half. if he declines, don't push it. if you do it again with a hotel, then you should pay for that time. bring extra condoms and a change of clothes.
posted by kerning at 12:27 PM on March 25, 2013 [3 favorites]

1. Yes it's a good idea, if you haven't been tested since your last sexual encounter (you never know if they had something, regardless of what they tell you). If you're meeting up in a week, though, you probably won't get the results back in time to know anything. Conversation could go something like "I got tested recently but haven't got the results back - I'll let you know if anything pops up. By the way when was your last test?"

I think it is a totally acceptable conversation and a good idea, but also pretty rare, depending on your demographic. I have never asked or been asked about testing before having sex - that tends to come up more in a relationship context. It is still a good thing to aim for though.

2. Not that much point in insisting on testing if he's actively having casual sex - STIs usually have an incubation time of weeks to months before they're detectable so a clean result doesn't mean he hasn't already caught something. It's still a good thing to ask about, of course.

3. Not really. Keep an eye out for suspicious sores, obviously. Otherwise (properly used, unbroken) condoms will protect against most anything except herpes and HPV.

4. No rules. Do what feels right and be honest and upfront as much as possible.

5. I'd suggest splitting the hotel (he might offer to pay which is also fine). Bring whatever you'd normally like to have for sex (multiple condoms, lube, toys if you want, etc). Maybe a change of clothes.

have fun!
posted by randomnity at 12:36 PM on March 25, 2013

Don't forget:::: Good lube that doesn't conflict with your condoms of choice! Water-based is always a good choice. Silicone is sometimes longer-lasting, but it's not good to use it with any silicone sex toys. If you're not using toys, silicone is fine. Get something without any sugar.
posted by barnone at 12:49 PM on March 25, 2013

you can ask him to get tested before you stop using barrier protection.

Please don't stop using barrier protection if this turns into a recurring hookup. I know condoms are a drag etcetera etcetera, but STD infection rates have been on a upward trajectory for a while now. If he is but a regular, sexy hookup, as opposed to someone you are in, you know, a committed monogamous relationship with, he is probably having sex with others, or would like to, or has that open as an option. That is not a scenario in which you want to go condom-free. Sorry.
posted by vivid postcard at 12:53 PM on March 25, 2013 [8 favorites]

Response by poster: Thanks so much for the suggestions and information so far!

Just wanted to pop back in with a few points:
1. He does already know that I've been celibate/monogamous for a long while, but I haven't brought up that I haven't been tested since six months after the last time I had sex (and subsequently received the all-clear)... which was a long, long time ago. I would never consider lying if he asked about it, I'm just not sure if I should bother running in and getting tested again before getting it on with a new person, if only because my last results were A-OK and I've barely even hugged anyone since then, let alone swapped fluids with someone.
2. I will literally never forgo barrier protection/condoms when I am with a partner with whom I do not have a monogamous/exclusive relationship. Ever. Total public health hazard, no matter how much it may suck and/or the other person may doth protest.
3. He is indeed actively hooking up with other people, having somewhat recently ended a long-term relationship. He was very open about this, told me right away, and we've had the "let's just hook up because neither of us wants a relationship but we're both really attracted to each other" talk already. So I'm thinking a mutual address of the whole are-you-testing/tested-or-not thing should probably be done before we even meet up.
4. Already had my favorite water-based lube, bunches of condoms, favorite toys, towels and a sheet (because I don't want to sully the hotel towels/sheets), and bottled water neatly lined up next to my overnight bag. Three cheers for advance planning.
5. I'm gonna offer to spring for the hotel, because I work for The Man and he's a bartender at a niche restaurant. We've spoken vaguely of switching off who would visit who if we kept seeing each other -- we live ~90 miles apart -- so if the hookups do continue, they'll be occurring in places that don't charge by the night, i.e. our respective abodes. (With protection. Always.)

Thanks again!
posted by electroshock blues at 1:40 PM on March 25, 2013

Ooh, the fact that you've had the "what do we want out of this situation" talk already seems to bode very, very well.

posted by EmpressCallipygos at 1:52 PM on March 25, 2013 [1 favorite]

It sounds like you're all set, but to be on the safe (maybe bordering on paranoid ) side, let a friend know your plans , and text him/her when you're back at home.
(have fun!)
posted by Fig at 2:23 PM on March 25, 2013 [1 favorite]

Regarding point 3: It's fine to skip oral sex, but I'm afraid oral with barrier protection is sex-educational fiction. Blowjobs with condoms don't really work, and while I can't say if it's the same with dental dams, that's because I never spoke with a single person who tried one.
posted by springload at 4:30 PM on March 25, 2013

Don't give him a BJ. You don't want to establish some infections in the throat. Risk is probably higher from a good looking bartender.
posted by discopolo at 5:27 PM on March 25, 2013

Response by poster: Multiple friends, including relatives who live within 10 minutes of where I will be, are already in possession of my intended plans, location, his name/contact info, history, etc. -- which is to say that if this all actually happens instead of just winding up forgotten as some silly fantasy half-concocted by weird strangers whose paths randomly intersected for a single evening, the safety aspect is pretty well covered. My Gift of Fear-dar somehow managed to invert whenever he was around, and at this point, I am confident in being able to ascertain from the type of man who might (or even could, theoretically) get scary in close quarters.

I am also aware of the risks and dangers inherent in this sort of activity, as I am aware of the risks and dangers of activities such as operating motor vehicles, drinking alcohol, having sex with anyone, and other stuff that can be, statistically speaking, even more dangerous than spending an erstwhile afternoon with a person you randomly meet and really like and just, y'know, wanna bang? That's a pretty good feeling to have, right -- not for everyone, but for some of us, yeah! Which is to say that I've been around the block more than a few times, albeit not in a very long while. And I promise not to get murdered.

Excellent tips and reminders for multiple aspects of maximizing your safe(r) casual sex practise -- just what I needed (and had forgotten over the years), cheers all!
posted by electroshock blues at 5:55 PM on March 25, 2013

i just wanted to add that condoms do not fully protect against hpv, so using a condom is not enough.
posted by TestamentToGrace at 8:09 PM on March 25, 2013

Response by poster: I got pinged with the auto-reminder to follow up, and didn't want any future AskMe readers to think I had been lost to the abyss of random hookups, so here I am!

We didn't end up going to a weird business hotel, we just went to his apartment -- after I had texted a half-dozen friends his address, natch -- and it was AWESOME. All other words fail me. It was simply one of the best, most fun, empowering experiences I've had as an adult woman.
After spending a fair bit of time discussing what we liked, REALLY liked, and might like to try, we spent ~12 straight hours running the gamut of all of the above. Disclosing STD testing status was not a big deal at all, just part of the pre-game checklist -- neither of us had any problem with asking or telling. Any/all acts were performed fully sober and only upon receiving wildly enthusiastic consent. I actually skipped to my car the next morning, and am still feeling pretty damn triumphant about the whole thing. We remain friendly and are definitely on the same page w/r/t future encounters (as in, "more of this, please!").

Long story short, it can be done! Communication, honesty, and safety are key! Good luck, fellow seekers!
posted by electroshock blues at 12:46 PM on May 2, 2013 [6 favorites]

« Older I have a few challenges applying to grad school.   |   What to do with a few hours in Moscow? Newer »
This thread is closed to new comments.