1. Quick & dirty question about online dating: What’s the best next step after texting? Audio message? Phone call? Video date? Or a quick, in-person meet-up?
I recommend a quick video call — a brief FaceTime chat — before that first brief, in-person meeting in a public place. If someone isn’t willing to jump on FaceTime to confirm their photos are current (and they’re not a fake, a flake, or a chatbot), they don’t deserve the pleasure of your company.
2. Help! I keep falling in love! With every female friend I have!
Maybe! You could stop! Using your dick! As a divining rod! When picking female friends!
3. We used to talk, my boyfriend and me. We used to share everything. Now I can barely get him to talk to me, to share things with me, to spend time with me. The more I ask him to spend time with me to talk and share, the more withdrawn he becomes. And forget about sex. How can I get our intimacy back?
You can only ask — and you have asked, repeatedly, and it sounds like the answer to all three of your asks (talk, share, fuck) has been “no.” So, it’s time to go.
4. Which is better: wrist cuffs or handcuffs?
By “handcuffs,” you presumably mean those steel law-enforcement-style restraints that snap around wrists, like these from Smith & Wesson. By wrist cuffs, you presumably mean those wide and ideally padded leather restraints that buckle around wrists, like these from Mr. S Leather. Handcuffs are effective, but they’re not comfortable or safe for play; if they twist, they can do nerve or bone damage (by design); and while some kinksters find their “law enforcement” vibes arousing, others are turned off by them. Leather wrist restraints, on the other hand, are far safer and far more comfortable for play and longer-term wear, and they give “depraved pervert” vibes, which many kinksters prefer.
5. There is this guy. Sometimes, it seems like he’s really into me; other times, he completely ignores me. Hot and cold. Push and pull. Clings then ghosts. What should I do?
Someone else.
6. I feel creeped out when a man refers to me as his “lover.” It makes me feel like Bill Murray in Ghostbusters: “I’ve been slimed!” Hearing that word applied to me makes me want to jump in the shower. But I don’t say anything because I know it’s supposed to be a compliment. What’s wrong with me?
Nothing. Lots of people have aversions to certain words — words that trigger feelings of irrational disgust — and “lover” triggers you the way moist, loins, panties, phlegm, and sputum trigger others. Personally, I always hated the word “nipple” when applied to me, so I was delighted when gay men started using “tits” about two decades ago. (They don’t give milk, but they’re still tits — tits in drydock, yes, but tits nonetheless.) Some possible alternatives for “lover” that your lovers could use when referring to you (in ascending order of emotional importance): cumdump, fuckbuddy, friend-with-benefits, significant other, boyfriend/girlfriend/enbyfriend, fiancé/fiancée/intended, husband/wife/spouse.
7. I am going to the Dominican Republic with my boyfriend for our anniversary. He is quite well endowed, and he wants to top me. How can I be a good bottom and anally douche in a country where the tap water is not drinkable?
They sell bottled water in the Dominican Republic — I checked — and as anyone who has ever left their douche bulb at home and had to improvise on the road knows, a squeezable plastic water bottle doubles as a douche bulb in a pinch.
8. I want you to put me in touch with the man who wants a submissive boyfriend willing to make the ultimate sacrifice for him and have his genitals removed. I would do anything to have a boyfriend, even if it meant making that sacrifice. Please send him my email address.
I am not allowed to put my readers in touch with each other — per my lawyer’s advice — but I can’t stop my readers from sliding into the comment thread for a particular column or podcast in the hopes of catching the attention of a particular letter writer or caller. But before you do anything rash: desperation is unattractive and nothing shouts “desperate” quite so loudly as, “I will cut off my cock and balls to land a boyfriend.” Boyfriends are great — I’m a fan of mine — but unless becoming a nullo is something you’ve always wanted to do for you, it’s not something you should do for “love.”
9. My boyfriend is depressed. Which normally, I can handle. I’m supportive as much as I can be. Except lately, now that I’m going through a rough time myself, I’m less able to be supportive. And I need him to step up and support me. He might not be capable of doing that, though. And the kind of support I need right now is that I need to feel wanted. I need to feel desired. So, if he’s having some low libido issues, what do I do?
You need to ask yourself how much longer you’re willing to stay with someone who — for whatever reason — can’t meet your emotional and sexual needs. Extenuating circumstances should always be taken into consideration, of course, and someone who ends a committed relationship at the first sign of trouble wasn’t serious about the commitment they made. But extenuating circumstances aren’t paralyzing circumstances, and a commitment isn’t a sexual and emotional suicide pact. If someone isn’t meeting your needs but is making a good-faith effort to get themselves to a place where they can, you should stick around. So, my question for you is this: Is your boyfriend making that effort?
10. Is it better to be very explicit/specific when it comes to planning an encounter that is going to be tricky to set up — advance planning, securing a hotel room, renting a car — or should you allow room for spontaneity? I have a feeling my possible partner will feel pressured if I start making these arrangements. But if we just play it by ear, it might not happen at all.
Make those arrangements but say this (say it and mean it) to your possible partner: “I’m gonna get a hotel room and rent a car in case we need them — but no pressure. If you’re not feeling it when we get together, or if I’m not feeling it, nothing has to happen. I’m pretty sure I would enjoy spending the night with you, but a night alone in a hotel room watching movies and eating room service isn’t a bad consolation prize if that doesn’t happen.”
11. I have mixed feelings about a guy, and I don’t know how to resolve them. On the one hand, I feel like he could be the love of my life, the best sex I’ve ever had, etc. On the other, I want to push him away, pull away from him, distance myself from him, etc. I keep writing breakup letters that I never send. Why do I desire him so much that he consumes most of my thoughts, and yet also want him out of my life? How do I know what I really want?
Could be a case of “right person, wrong time,” i.e., he’s someone you could see yourself committing to but you’re not ready to make a commitment, or your Spidey senses could be picking up on something you aren’t able to see and/or can’t quite articulate. This is a good time to call in your besties — supportive friends, not underminers — and ask them to be brutally honest with you about what they think of this guy as a person and you two as a couple.
12. Best place to meet ENM people in 2024?
As much as people like to complain about dating and hookup apps, they’re still the best place to meet people with niche sexual interests and/or an interest in non-standard relationship models, e.g. open, poly, toly, monogamish, swinging, DADT, stag/vixen, cuck/slut and all the other forms ethically non-monogamous relationships can take.
13. I last too long and want to be able to come easier. I don’t use a “death grip” during JO. Any advice?
Fire on all cylinders: in addition to direct stimulation of your dick during penis-in-vagina/penis-in-butt/penis-in-whatever, toss in some tit play (if your tits are wired), shove in a butt plug (if your ass is in play), add some dirty talk (if you enjoy it), etc.
14. How do you know when it’s time to open a relationship?
When you’ve talked with your partner about opening your relationship and you’re both in agreement — that doesn’t have to mean you’re both happy about it (some people open things up under duress), but you both have to be on board. That is, if you wanna practice ethical non-monogamy.
15. Bi guy in relationship needs dick. I’m in my 50s and want to explore. How do I get started?
First, secure partner’s permission to go and get some dick (unless you’re in a DWYNTDTSMASS situation). Once you’ve got it, take some pics (accurate ones), download some Sniffies (or Grindr or Scruff), get some dick (it’s really that simple).
16. In a situationship of sorts. It’s been over a year. I don’t know what kind of future we have, and he’s been unable or unwilling to have that sort of conversation. He will instead make comments about how he doesn’t want to overthink, over-scrutinize, do any emotional labor. How do I get clarity here?
The problem here isn’t a lack of clarity — he’s made himself clear — it’s wishful thinking. He doesn’t want what you want, e.g., a defined relationship, a commitment, the emotional and social obligations that come with a commitment. And right now, he’s getting what he wants, i.e., full use of your holes, because you’ve convinced yourself he’s being unclear when he’s not. DTMFA.
17. Can I think of myself as sex positive if I don’t want to have sex? In the general gay utopia (which seems very sex positive), where does someone like me fit in? A bit of background information: I am a 32-year-old male. I was raised Catholic but no longer believe. I am currently in counseling.
If someone with a hundred sex partners a year can think of themselves as asexual — and I recently met a self-identified “slutty ace” — I don’t see why someone who doesn’t wanna have sex can’t think of himself as sex positive. And it’s less of a reach because being sex positive doesn’t mean having sex whether you wanna have it or not. It’s about seeing sex as a positive good (not just reproductive one) and giving yourself permission to make the right sexual choices for yourself — which can include the choice not to have sex — and letting other people make the choices that are right for themselves.
18. Is there a reason that only guys who are in relationships already are interested in me these days?
When you were a younger gay man — you submitted your question via Instagram, I checked out your feed, you’re a gay man — most of your peers were single and available. Now that you’re a bit older, your peers are likelier to be partnered. But since open relationships are the norm among gay male couples, they’re still available. So, the pool of single-but-available men who are interested in you has shrunk while the pool of partnered-but-available gay men that are interested in you has grown.
19. Why can I only come when stimulated with my vibrator and not when I try to do it by hand?
Could you come by hand before you got a vibrator? Well, then you may have developed a physical or psychological dependence. If you couldn’t come until you got a vibrator, you may be one of those women who can’t come without the kind of intense and deep stimulation of internal clitoral tissues that only a vibrator can provide. If you’re in the former camp and it bothers you, you can try giving up your vibrator for a while. If you’re the latter camp, you should get down on your knees every day and thank God for that vibrator of yours.
20. Where the hell are my keys?
My husband asks himself the question two or three times a day. And his keys are always right where he left them… it’s just that he never leaves them in the same place twice. So, my husband got one of those remote-control-activated alarms for his keychain that emits a piercing shriek when he presses a button on his phone. It’s a system that would work perfectly if he ever put his phone in the same place twice.
21. What’s the best way for a gay man in his 60s to meet men to date?
The same way everyone else meets people to date — sign up on the dating/hookup apps, join clubs, volunteer, leave the house, go places, do things, meet people, fuck the ones who wanna fuck you, keep fucking the ones who wanna keep fucking you. Good luck!
22. Is it normal for the prostate to swell up a lot after orgasm? Like, levels of swelling that make it hard to sit afterwards.
It is not — could be a sign of prostatitis — and you should go see your doc.
23. Why does it make me SO hot when my partner says he’s proud of me during sex?
Praise kinksters are real kinksters — plus, if you were raised in a sex-negative household and/or in a sex-shaming faith, hearing your partner say he’s proud of you for getting his cock all the way down your throat can be equal parts hot, healing, and affirming. Ask me how I know.
24. Should I throw out my collection of clothes I stole from people I slept with for my new partner?
I don’t think you’re asking yourself the right question.
25. How do you handle a low-libido sub when you are a gentle Mommy Dom who wants it more?
You supplement the sub you have with other subs and/or you order your sub to read the column I wrote about assisted masturbation — one way a low-libido partner can help out a high-libido partner — and incorporate assisted masturbation sessions into your repertoire.
26. What’s your ball trimmer recommendation?
This will do — wait, are we talking about trimming balls or trimming pubes?
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