Playboy Undercover: Diary of a Simp

"I’m a simp. And that’s sort of a statement of fact, like 'I’m a nerd' or 'I have a very mild benzo problem.'”

Sex & Relationships June 3, 2026
Charlotte Rutherford

Welcome to Playboy Undercover—where our anonymous columnists give you a peek of what’s really going on, well, under the covers. From the curious to the downright kinky, our guides are pulling back the curtains on desire. Wanna invite us undercover? So long as it’s between two (or more!) consenting adults, we’re game. Send your story to [email protected].

I think “simp” has two definitions: the first is basically “someone who pines for someone they have no connection to,” which isn’t new, and “someone who goes to lengths to maintain a parasocial relationship with someone desirable,” usually financial, and this is much more common in the age of social media. One is a crush, and one is a more complicated relationship that is (slightly) less one sided. 

I’ve definitely had unrequited crushes and such, but it wasn’t until I was actually buying clothes for a girl from Twitter in order to talk to her where it suddenly clicked, “oh, I’m a simp.” And that’s sort of a statement of fact, like “I’m a nerd” or “I have a very mild benzo problem.” It’s not something I’m proud of or would freely admit, but there’s no point in denying. And I enjoy being a simp, just as I enjoy doing nerdy things. If someone were to say about me, “oh, he’s a simp,” I’d just have to shrug my shoulders and agree.

It’s entirely digital, though maybe that would be different if I were younger. As for my daily life, there are a few women I’ve simped for longish term that I’ll check in with once or twice a week, I’ll send money to them, get pics from them. It’s sort of an extension of using social media in general. I have friends from high school I occasionally talk to through IG, and I have women I simp for who I occasionally talk to through IG (or Twitter in the past) though there’s a sexual element, of course.

It’s much much easier to initiate digitally, and it’s also much easier to connect with “highly desirable” women online; you just DM a girl something flattering after they post a selfie and offer to buy something. “I’ll buy you clothes if you send me pictures of you in them” is a very common simp transaction, and was my first experience with it. 

The first girl I really was an online simp for (sending money, liking all her posts, commenting, etc) was a Twitter e-girl who posted some lewd photo of herself. I drunkenly DM’d her to tell her how gorgeous she looked, she thanked me and told me one of her simps bought her the outfit, I offered to buy her another outfit. That progressed into a consistent thing of me sending her money in order to converse and sext, more or less. Eventually things did get a bit emotional and messy, and we took a break before she returned with a more domineering attitude.

Michael Folkes

But my first experience with the dynamic in general was in college, where a girl from high school I was friends with (and occasionally did PG-13 stuff with) said she wanted a pair of athletic shorts for her birthday. I bought them for her, and when she said she got them I asked to see them on her. And that kind of has been the most basic element of simping since then; paying for things in exchange for seeing them be used.

It is definitely a secret part of my life, though it still is more or less a daily part of it. I think a lot of people have more compartmentalized lives since the pandemic, but probably not to this extent. I also think it’s more dignified than the people who comment under porn star posts on their main account. 

It seems intuitive and obvious to me that the internet lets us express ourselves in ways we wouldn’t feel comfortable doing in person. Anyone with a finsta should understand the concept of there being multiple selves, some of which are better kept hidden. The concept of a shadow self isn’t really new, but we’ve never been able to so casually swap in and out of it. Who we are on the phone isn’t who we are at dinner with our family. 

So while the “real” me values being confident, interesting, desirable, etc, the “phone” me has no problem indulging my id’s desires. It’s like how one might order a grilled chicken breast with seasonable vegetables when at a restaurant, but on DoorDash might get a triple decker fatty burger with extra cheese. Similarly, if I were on a date with someone simp-worthy, I would dress well and talk about places I’ve traveled and my cultivated tastes, but on the phone I have no problem begging that same woman for the privilege to buy her lingerie.Because phone me and real me are completely different!

I think I’m relatively normal in my daily life, if a tad neurotic. Cosmo Kramer by way of George Costanza would be an acceptable comparison. I have a social life, I’m in a normal relationship, I have fulfilling hobbies. I’ve done my share of coke in bar bathrooms with performance artists. I’m a neurotic hipster doofus with too much money and an Ivy League degree. I honestly consider myself vastly more cultured than the average American. 

Because of that, I think having my simp self revealed would be a bit disastrous. My friends would lose respect for me and I’d probably be invited to less events. People’s perception of me would instantly turn towards pathetic. Any unique traits of mine would be overshadowed by “simps for women online.” It’s more interesting gossip than anything else about me.

Who we are on the phone isn’t who we are at dinner with our family. 

That feels like the main change. People would view me as a simp before anything else

I’d guess I’ve roughly spent around $15,000-$20,000 simping for women online.

I do sometimes feel a sense of shame about it. It’s kind of akin to a hangover. Thinking to myself, “I’m going to regret this later,” and guess what, I do regret it, and I question my life choices and feel down about myself. HOWEVER. This is pretty quickly alleviated by living my normal life and remembering that I do have quite a bit of good things going for me. 

I think I’m the sort of person that requires some sort of self-destructive element in my life. The basic elements of being a simp are there whether I like it or not; I’m attracted to women out of my league. Most men are! But the way I choose to indulge those elements, and feel the shame and regret and embarrassment that comes with it, is sort of a luxury. I can do these stupid things and humiliate myself because it doesn’t hurt me in the long run.

“Pain can be a positive thing” is one of my favorite truisms. And, I can afford, financially and emotionally, to experience this unique pain. My broader point is: yes, I certainly feel shame, and that’s both part of the fun and part of some weirder regulatory thing my mind does to remind me to appreciate the normal things. The inherent disappointment that comes with paying women to acknowledge me makes me more appreciative of my normal relationships. 

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