Just the Tip: Overnights and Older Women

Just the Tip offers smart and compassionate sex and relationship advice from queer non-monogamous kinkster Jera Brown. If you have a sex or love question you’d like Jera to answer, email  jera@jerabrown.com or DM Jera on Twitter @thejerabrown.

Ever since my last serious relationship, I’ve missed sleeping next to someone. I’m casually dating, and I don’t want anyone to get the wrong idea if I ask them to spend the night. Can I get this need met without someone expecting I’m ready for a serious commitment?

If you’re already sleeping with someone, do you have an idea of what they think sex means? Have you talked about whether you’re FWBs, casually dating, or getting to know each other to see if something more serious will develop? I get that you might not be ready to rock the boat by having this kind of conversation, but I personally believe the earlier you have this conversation, the better. Hopefully you’d rather lose out on sex than hurt someone’s feelings by leading them on if you’re not on the same page.

Some possible openings:

“This might head somewhere, but I’d like to take it really slow. I like where things are at right now. How do you feel?”

“I really love being intimate with you, and I enjoy your company. I see you as an affectionate friend that I care about and wanted to make sure that’s OK with you.”

Once you’ve established you’re on the same page about what the thing is between the two of you, then you can bring up something like overnights without a bunch of vague expectations of what it might mean.

I’m 23, and I like older women. Like twice my age. I’ve always been into them. How do I get them to take me seriously?

I’m going to assume you’re not just looking for a mother figure to take care of you and that you’re not just looking for sex. Otherwise, it’s difficult to answer why someone would take you seriously.

If you’re looking to date an older woman, the key is to demonstrate your maturity. You don’t have to pretend to be older than you are—that sets up a stressful and inauthentic relationship. But if you want to be taken seriously, prove that you take both her and yourself seriously.

When you communicate, be thoughtful about her interests, career, family, etc. Ask a lot of questions and give thoughtful compliments. What stands out about this woman?

Prove that you’re mature for your age by discussing and displaying your ambitions, your ability to take care of yourself, and so on. I think most women who are open to dating someone your age are going to be looking for signs that you’re her equal: anything from having a clean bathroom to being able to talk about things on a deeper level.

And when they’re not interested, don’t feel like you’re doing something wrong. Just like you have a preference, maybe they do as well.

Jera writes about sexuality, spirituality, and social justice. They are the author of Just the Tip, a queer-friendly, sex-positive, relationship advice column and the editor of Sacred and Subversive,...