How to Do It

I’m an Older Woman Dating Again, and I’m Not Sure How to Ask Men About a Little Sexual Issue These Days

An older woman next to a small eggplant emoji.
Photo illustration by Slate. Photo by Siri Stafford/iStock/Getty Images Plus.

How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!

Dear How to Do It,

I am an older woman who has recently gotten back into the dating game. My problem is I hope going to be fun for you. Ha ha. So I am a semi-conservative woman and am hoping to meet someone similar. But I also am very sexual. I have only been intimate with one man since dating, and I was thinking he could be the one, but when we decided to play, I was very saddened to find he had a very, well, micro problem. Literally to where sex was not possible in the traditional manner. And never could be. I ended the relationship, this being the main reason. I know there are other ways to get it, but I want that. So, my question is, what would be a tasteful, respectful way to inquire or find out about size? I don’t need a horse, just a functional man. I am mature enough that I was able to discuss sex with him before we met, told him how important it was to me, and we even had some fun sexting where he described sexual positions and thing he would do with his boy that he KNEW he couldn’t do!! So I was angry about that.

—No Surprises

Dear No Surprises,

I’m of two minds about this question. I feel a little bit shitty about advising on how to avoid micropenises, as their owners already face enough rejection as is. (And I’d steer you away from implying those guys aren’t “functional men.”) But I also think that the guy with the ironically big surprise in his pants that you encountered should have told you upfront what he was packing, especially since you discussed sex openly and he seems to have deliberately misled you. The expectation for traditional intercourse is reasonable and anything that would obstruct it, I think, is best discussed beforehand. On top of this, I’d be a hypocrite if I pretended like I didn’t partake in the hunt for a meaty dick myself. It’s one of my favorite sports, even.

I’m going to get a little Sex Tips for Straight Women From a Gay Man on you for a second, so pardon my triteness. Here is how men who have sex with men tend to broach this conversation: They inquire directly. On apps this might mean saying, “How big?,” or “How hung?” It might not even require asking as the other party may have started the conversation with a picture indicating exactly how big he is, or it’s already in his profile. Easy. I know things can be more complicated in conversations between men and women, but the casualness with which this is handled by queer men just goes to show that it doesn’t have to be.

Naturally, not everyone is comfortable with this conversation, but those who have the most problems with this line of questioning probably have the least to offer, size-wise. Sometimes a nonanswer is an answer. As long as men are carrying their sense of self-worth in their underwear, this will always be a delicate matter that exists outside of the realm of polite conversation. You can take some of the edge off by approaching the subject with humor—you can off-handedly mention that your friend calls you a size queen (in this case, I am your friend and I’m calling you a size queen). You can hint in your online profile that you’re looking for someone who “measures up.” I understand that this doesn’t jibe with your conservative image, but look, if this is a big enough concern of yours to warrant preemptive inquiry, maybe you’re not as conservative as you think you are.

Beware, though: People lie about their penises. I’ve had a guy tell me he was eight inches, have sex with me, and then after, repeat that he’s eight inches. I wondered if he measured starting at his butthole. Ultimately, you can never really be sure based on word of mouth alone. A dick is something you must experience to know what it’s like. Fortunately, there is a lot of joy in discovery.

Dear How to Do It,

I’m a single guy, middle-aged, and I’ve always identified as straight. I indulge in porn, but mostly women in bikinis or nude, showing a lot of skin and curves. I don’t like the hardcore stuff. But about a year ago, I saw a video with a bikini girl and a guy in a speedo. I was surprised to discover that the sight of the guy turned me on! After, ahem, investigating a few more videos, I realized it was all that bare skin that was turning me on. Smooth, bare skin—no hair, no tattoos. Man or woman. I don’t want to have sex with a guy: no oral or anal. But I do fantasize about making out with a guy, kissing, and feeling each other up. Even in my fantasies, I balk at going below the waist. I think that if I were actually with a guy, I’d be OK with using my hand down there, but not my mouth. My question isn’t whether this is weird (it’s a kink, who cares?) or whether this makes me gay or bi—I don’t care about labels—but really: How realistic is it to find a guy who would be content with just making out? I mean, “First base? Yay!” “Second base? Woo hoo!” “Third base? Ooh, look at the time … gotta go!” Who would put up with that?

—Skin-tillating in Salt Lake

Dear Salt Lake,

For as long as there have been curious straight guys, there have been queer guys to indulge them. Do people tend to advertise that they’re only going to go as far as first base on Grindr? Not typically. Are guys who fool around with guys looking for jerk-off buddies? Yes, frequently. It sounds like that’s what you’re looking for, even if you’re somewhat reluctant to state it outright and had to basically tease it out of yourself. I think the important thing to do here, no matter which venue you choose to pursue, is to be upfront and honest about your desires and boundaries. People argue that the fixation of some queer men on turning straight men amounts to self-loathing, or at least a deep investment in heterosupremacy. This may be so, but I think you’ll find no shortage of guys who will want to show you the ropes, and on your terms—for better or worse. Enjoy that while you can.

Dear How to Do It,

I’ve been out of a three-year relationship for a little more than three months now, and for better or worse, I was the one who was dumped. I was told the main reason was that my partner was no longer sexually attracted to me and had feelings for their ex, who was a part of our mutual friend group. About a week after the split, my ex and her old ex were back together as FWB and spending almost every day together 24/7. I’m so at a loss as to how to recover. I’ve been seeing a therapist when I can and trying to be active outside of school and work. I just feel so crushed and lacking in the sex department, because I was told I am bad at sex and then let go four months after we had moved into our first place together. The bonus is that I still work with my ex and we are in the same college nursing program for the next two years, so I will see them every week at least once or twice. I am afraid to try and put myself out there and I don’t want to let someone else down sexually, even if it’s casual. Also, how do you even be sexually casual?

—Casually Confused

Dear Casually Confused,

Assuming you consummated your relationship before moving in together, you weren’t bad enough at sex to prevent cohabitation. Moving out four months after moving in with someone and blaming it on bad sex is reckless enough to make your ex an unreliable source. Something else is going on. If you somehow offended them, saying you’re bad in bed may be retaliation; if completely unprovoked, it’s sadistic. Regardless, “bad” tends to be in the orifice of the beholder—generally what “bad sex” comes down to is a lack of chemistry, something that is unique to every pairing. (On a more objective tip, selfishness and a complete disregard for a partner’s feelings and pleasure also can cause “bad” sex—but again, that impacts chemistry.) This is to say that if you are considerate, generous, willing to learn, and invested in your partner’s pleasure, you’ll find someone with whom you click.

Recovering from this may take time—do whatever you need to help yourself heal, including ignoring your ex entirely. Not everyone is built for casual sex, and luckily, it’s not required. If it seems foreign or even impossible to you, it may not be for you. It sounds to me like you should be pursuing meaningful connections with potentially serious partners. There’s absolutely nothing wrong with doing so.

Dear How to Do It,

I seem to have backed myself into some kind of hooking-up corner, and I am not really sure how to navigate it. Currently, I am hooking up with two FWBs for the past few months—think a Tuesday and Friday night guy with an occasional extra date thrown in. They are aware of each other and I have gone to one’s house with another’s hickey still on my chest. Neither seem to want more than to hook up a couple of times a month, and I want (feels like need) the physical contact. It’s concerningly the only thing that seems to get my serotonin off the floor these days (yes, I see a therapist). I was in a long-term relationship until early this year and would like to be exclusive again, but I need someone who can give me attention a couple nights a week. I passively swipe on the apps and go on the occasional first date, but anything less than relationship material doesn’t pierce the fog because I already have FWBs and don’t want to create a harem of fuck buddies at this rate. Short of abstinence, because I am very into pleasure, how do I navigate and move forward so I can get everything I need from one person and not a little bit from multiple? Is that unrealistic, and I am clinging too strongly to society’s boner for monogamy? Am I actually here just looking for your permission to have at it? (if it helps your judgment, I am straight woman in her late 20s).

—Hookup Haze

Dear HH,

None of your FWBs are that guy for you. You’ll know you’ve found the one when you both want to spend a (roughly) equal amount of time together and focus on each other, at least for some length of time. The way to find him is by doing exactly what you’re doing. As long as it isn’t bothering you, I encourage you to keep wandering. It’s OK to want just one guy—whether you’ve been indoctrinated or arrived here biologically, it’s what you are after at this point. You like what you like.


More How to Do It

My husband and I have an amazing relationship, and I love him deeply. A few months ago, at my suggestion, we started trying threesomes (with another woman) and have really enjoyed it so far. It’s brought us even closer—it’s given me a chance to explore that side of my sexuality—and it’s been a really fun and positive experience. One of our boundaries concerns his orgasm, which we decided from the beginning should always be with me. It just felt like a more intimate thing, and it hasn’t been an issue until our most recent encounter. The other woman and I had spent quite a bit of time teasing him, and he wasn’t able to hold back when he was inside of her. He feels absolutely terrible, and I understand how it happened, but I’m now feeling uneasy. I feel like my trust has been broken, but it was an accident, and I’m not angry, just on edge. There’s nothing to be done about the past, but I’m trying to process how to move forward and also not spend our next encounter worrying about it happening again. Any advice?