By Dan Savage - Oct. 10, 2024

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 in the relationship. How do I get clarity here?

The problem here isn’t a lack of clarity on his part — he’s made himself clear — it’s wishful thinking on yours. He doesn’t want what you want, e.g., a defined relationship, a commitment, the emotional and social obligations that come with a commitment. 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. 

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 or 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 their commitment. 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 an effort to get there?

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 (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 love to spend the night with you, but a night alone in a hotel room watching movies and eating room service isn’t a bad consolation prize.”

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.

I last too long and want to be able to cum 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), toss in a butt plug (if your ass is in play), toss in some dirty talk (if you enjoy it). 

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.

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