Dating as a Divorced Man Is Easier Than I Ever Could Have Imagined. But One Thing Is Making It Difficult.

Our advice columnists have heard it all over the years—so we’re diving into the How to Do It archives to share classic letters with our readers. Have a question? Send it to Stoya and Rich here. (It’s anonymous!)

Dear How to Do It,

I just got divorced after a marriage that ended miserably. Sex went away, then she started sleeping with a neighbor. She skipped the therapy, and eventually moved out. Now I’m in a new world. My 18-year-old self would never believe how easy it is to get laid. The third date rule has gone out the window. Dates are cut off in order to go home together. One woman drove across the state and invited herself into my bed. The version of me that spent his 20s drinking up the courage to find women at the bar would not believe the stories of the mild drinker having one-night stands with women at restaurants.

Or trying to. There are maladies aplenty. The sex often seems perfunctory and chore-like (I’m still getting compliments, so I guess they thought it was OK, or are very polite). My dick just isn’t showing up for the job frequently. I find the women tiring, exhausting, and time-consuming, and I find myself thinking of how to get out of these situations and get my house back to myself. I put on weight initially, but lost a good chunk. I have a stressful job. Is sex gone? I like the idea of sex conceptually. I still find women attractive, but the urge to do anything about it seems to have dissipated. Nudity in movies is still exciting. I can get the dick to show up at home, but the conditions have to be right and it doesn’t want to hang out like it used to. It weighs on me when I meet women. It’s embarrassing to have considerate women trying to get you erect, and you have nothing to show for it. How do I get excited about sex again?

—Not Working

Dear Not Working,

A few things spring to mind. You might benefit from a long break to reset. Put sex on hold for what feels like a substantial amount of time for you—say a month or two, maybe. See if absence makes your dick grow harder. When sex is plentiful and routine, it can become unexciting. We stop yearning for that which we have in abundance. There is thrill in scarcity. At minimum, choose your partners with a bit more discernment and experiment with not jumping in bed right away. See if an extended flirtation will help edge you toward full engagement.

You don’t reveal how old you are, but I get the sense that you’re middle aged, and often in that period, testosterone levels sag, dragging down your libido in process. If you haven’t discussed this with your doctor (GP or urologist) and/or gotten bloodwork recently, do so. Specifically ask to have your T levels checked. If they’re low, you may benefit from testosterone replacement. Taking T in this day and age is fairly commonplace for men as it’s easier than ever to obtain via online platforms that tend to be permissive with prescriptions. Given the risks that come with supplementation like shrinking testicles, blood clots, and sleep apnea, I’d follow the guidance of an IRL doctor if you go that route. They tend to be a bit more judicious and can examine you more closely than someone that you only meet with virtually, if at all.

Finally, consider direct action on your ED like PDE5 inhibitors (sildenafil or Viagra, tadalafil or Cialis, and vardenafil or Levitra). A cock ring may also be useful (though be careful not to wear it for longer than 30 min). While these treatments don’t target the libido, they can have residual effects on it. A few instances of going soft can imbue sex with anxiety that makes the entire ordeal less attractive. If you have some help with your wood, that can assuage your anxiety and make sex much easier to get lost in.

I’d try a combination of all of these things: get your levels checked, slow down on sexual stimulation, and when you do connect that way with someone, pop a pill and/or wear a cock ring. If this doesn’t work, consider counseling or a sex coach.

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Dear How to Do It,

My girlfriend and I (he/him) have a pretty regular sex life, but we had a bit of a dry stretch a few years ago due to external factors that caused us to be less interested in going at it. When I would tease or try to initiate having sex, my girlfriend would often turn me down. Nowadays, we’ve cleared those external hurdles but I find it hard to get over my mental block about initiating. Even though I know things are better, I always find myself a little too scared that my girlfriend’s going to say no, and I think it’s impacting our sex life negatively. I’m just not sure how to move on.

—Hesitant Initiator

Rich Juzwiak
I Think My “Alone Time” Sex Habit Is Fine. My Friend Thinks It’s Deeply Sinister.
Read More

Dear Hesitant Initiator,

Have you talked to your girlfriend about this? It might help if she initiated more. It would reaffirm her interest and take some of the pressure off you. It’s one thing to know that the past stresses are no longer burdening you, but it’s another thing to actually feel your partner’s interest. If she is less inclined to initiate, you should encourage her to express her sexuality freely, maybe sharing fantasies or telling you when she’s feeling particularly horny. If you let her know that you’re still feeling insecure about the past, she may step up and provide beyond what she’s naturally inclined to.

If your dynamic feels fixed and you are the designated initiator, just give it more time. You’re unlearning a pattern. Hopefully with positive reinforcement you’ll eventually see that your solicitations won’t be rebuffed every time and you’ll fall back into more frequent sex. Rejection can sting, but it does come with the territory, even with partners. Understand that no matter how far you’ve come, getting rejected will always be possible. Not everyone’s libido can line up with their partner’s perfectly every time. Making peace with the permanent possibility of no would serve you well.

Dear How to Do It,

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I’m a Sex Worker. I Had a Client So Good in Bed That I Want to Do Something Unprofessional.

I’ve got a simple question and I don’t think I’m worried about it since I’ve never had a problem. The head of my penis is numb; is it supposed to be that way? I get plenty of sensation around the head and down the shaft. I’m uncircumcised, so I’ve not had a medical accident. I was with someone who expressed surprise that my head was numb and, having never missed anything before, I was just curious if all or most possessors of penises also have numb heads.

—Unfeeling

Dear Unfeeling,

For many people, the head of the penis is the most sensitive part. But! This does happen—someone wrote into this column a few years ago (also uncut!) who also experienced a numb glans. I consulted a urologist and he told me when he observes this in patients, it’s most often psychological. He did raise the possibility of something like spinal cord lesions, which could only be confirmed by a doctor. Nerve damage is often cited as a cause of penile numbness. Low testosterone, diabetes, multiple sclerosis are other potential causes, as are some medications.

You say this doesn’t cause you problems and that you otherwise have sensation in your penis. Perhaps this is just the way your body is wired and nothing can or should be done. But if you want to be extra careful, talk to a urologist about it. That’s what I would do, just to be safe.

—Rich

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