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I’m Trying to Date Again After Back-to-Back Negative Experiences

What should I be asking myself as I begin to form new attachments, especially after showing such bad judgment in the recent past?

I’m trying to date again after back-to-back negative relationship experiences. Experiences that have made me question my own judgment and ability to set good boundaries. My friends and therapist all pointed out the red flags, but I was apparently blind to them. I love what you’ve said about how there is no “The One” out…

I Don’t Want to Fall into a Daddy/Boy Dynamic Accidentally

How do I date him like I would someone closer to my age and income?

I’m a 31-year-old queer person living in Europe. I recently met a 46-year-old man. We were visiting the same city for work and met on an app and went on a series of amazing dates. We have a lot of similar interests and work in parallel fields. Now we’re planning a trip to see each…

My Wife Recently Caught Feelings

She stays at her girlfriend’s place one to two nights a week. I get jealous and sick to my stomach when she is over there.

Straight guy here in a one-sided open relationship. My wife and I opened our relationship just for her and to females only so she could explore her bisexual side. I’m super proud of her for coming out and wanted her to feel fulfilled. When we agreed to this, I was naive and figured anything she…

I Have a Problem When I Have Sex or Masturbate

I have consulted several gynecologists, but no anomaly or infection of any kind has been found.

I am a 29-year-old woman, and I have a problem when I have sex or masturbate. I always feel an annoying pain, a stinging sensation in my vulva, at the entrance of the vagina, that does not allow me to enjoy it, as the pain is too overwhelming. Unfortunately, this situation has led me to…

Do I Take the Plunge With my Much-Older Boyfriend?

It doesn’t seem fair to have a child with a man who is almost 70.

I have a problem. (How’s that for an opener?) I’m a 60-something cis woman with a 30-something cis man lover. The problem is my vagina is extremely tight. Also, sometimes I bleed a little bit after PIV and then urinating burns, but only briefly. We are only able to hook up about every other week, so…

I Want Being Poly to Be Something That Makes Life Amazing!

But I am still being restricted by silly feelings put in my head via some nefarious patriarchal capitalist hack.

I’m a 34-year-old straight cis male. About 18 months ago, I met a lovely human that I’m crazy about. When we started dating, she said she needed us to be poly, and I agreed. It was a first for both of us! I’d always been interested—my parents are queer and have been poly my whole…

How Much Cum Is Safe to Drink?

Could you contact a doctor for me?

I’m a 40-year-old bi guy, and I’m really into drinking cum. I say “drinking” and not “swallowing” because I’m talking about glassfuls. I make and sell videos of me drinking large amounts of cum. Since I don’t have a stable of guys to supply me, I use frozen cum. It used to just be my…

This Isn’t Your Typical Bisexual-Person-Married-to-a-Straight-Person Problem

I feel like I’m losing out on a ton of intimacy with my husband by not being in the moment with him while I’m trying to come.

Longtime reader here, first-time writer. I’m a bisexual woman. I’ve been married to a straight man for eight years. Our marriage and our sex life are amazing. We communicate well, and we have a lot of fun together. You probably think you know where this is going, Dan, but trust me, this isn’t your typical bisexual-person-married-to-a-straight-person…

My Whole Life I Have Wanted to Be Spanked by Older Men

Does this make any sense?

I’m a straight guy but my whole life I have wanted to be spanked by older men. Does this make any sense? Because I’m confused. I don’t like or want penis, yet I want to be spanked as a punishment by men. I don’t understand myself sometimes. —Sincerely Pondering And Not Knowing The truly important…

At What Point Do We Spill the Beans About Our OnlyFans to our Friends With Benefits?

Do our FWBs have a right to know? 

My wife and I are in a great ENM marriage. We have two couples who we are friends with and get together regularly with for sex, and we each pursue solo FWB relationships. During COVID, we started posting pictures on Reddit, which were well received. This morphed into my wife starting an OnlyFans account because…

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