How to Do It

I Want to Find Love. But Only With a Very Rare Type of Man.

Preferably one on the, er, smaller side.

A nude woman holds her hands in front of her genitals/ private parts with a neon pink ouch hurting sign above.
Photo illustration by Slate. Photo by VladimirFLoyd/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’m recently divorced and in my 40s. I’m wanting to love again, but I have chronic pain in my core muscles from doing everyday things like standing. This means penetrative sex can be painful. This was an issue with my ex and was a big reason why we split. I have only ever experienced pleasure from clitoral stimulation. Penetrative sex became more painful after the birth of our son. When I separated from my ex I was briefly involved with a man who was self-conscious of the small size of his penis, but with him, I was comfortably able to get clitoral stimulation during penetration without pain, which enabled a deeper level of intimacy. Now, as a single woman looking for love, how do I broach this? No one wants to hear early on in a relationship that penetrative sex might be off the table.

Also, how even could I vet potential suitors by their penis size before it’s already gone too far, emotionally? Everyone who swipes right on all that is going to be a weirdo. There is a man I have been dating but I have had a particularly bad bout of pelvic pain recently and I can’t help but think having sex with him has aggravated it. I enjoy his company but I have started to fear meeting him as I know we will want to have sex and I don’t feel I can face the physical repercussions after. I have had to reduce my hours at work as my pain is so severe. I have had regular, expensive and invasive osteopathy treatments for years but that is not helping so much anymore.

All this is making me feel like I cannot even try for love in my life, and I’m not sure I can make peace with that. I have lots of good friends, but if I have to live the rest of my life in pain and shunning love, I am not sure what the point is. I feel very old. I have my son, whom I adore, and the time with him is worth carrying on. But being on my own is a struggle, and he will grow up soon. How can I approach this?

—Physically Painful Finding Love

Dear Physically Painful Finding Love, 

Your pain and frustration are palpable, and I have sympathy for you. Be gentle with yourself—you, like everyone else, deserve love. And that’s not even in spite of your health issues. An attitude like, “Everyone who swipes right on all that is going to be a weirdo,” is self-defeating. Firstly, many people who swipe right on anyone are weirdos (sometimes the good kind, sometimes not). Secondly, you don’t have to provide your medical history and charts in your profile. You don’t have to have sex with these guys (especially not initially) or even suggest it’s on the table. You can just get to know people. You have more to offer than your vagina, right? Lead with the other stuff.

Similarly, you said no one would be interested if penetrative sex was off the table. I beg to differ: While they may be less common, plenty of guys don’t want or need penetrative sex, and would be perfectly happy keeping that off the menu, especially if there were other ways you could be intimate. PIV is not all things to all people. There is, of course, a wide spectrum of sex to be had out there—oral, manual, kink, BDSM, tantra, etc. You could also be forward on apps regarding what you’re willing and unwilling to do and see if you can find takers.

When it seems like a relationship has progressed enough that sex should be part of the conversation, then you can disclose your issues. You may find yourself in the company of someone who likes you for you enough that he’s willing to explore what your body is capable of. The idea is to find someone who will accept you as you are, and not someone who is looking for you to be his sentient sex toy.

If you’re truly in the market for a small penis, there is a dating site purportedly catering to the un-endowed and their admirers, Dinky One. Can’t say that’s my bag at all, so I don’t know how it is, but it got some press a few years back and still exists today, so perhaps it is effective in circulating small dick. It’s another option, as is being straightforward in your other profiles about preferring smaller endowment (which I think would make some men very happy to read). I think you have quite a few solutions here—life is frustrating enough without adding defeatism on top of it. Don’t get in your own way and hold onto hope.

—Rich

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