Rip van Dinkle…Just a Regular Dude Famous For Having a Small Penis

In April 2017, I wrote a post PENIS SIZE: does it really matter? What women really think. In that post, I discussed average penis sizes, men’s concerns regarding their penis size, and what women really think about penis size. Penis size is quite the popular topic in our society and fortunately, I was able to interview a man with a small penis.

Rip van Dinkle

“Rip van Dinkle” is the alias used by a Minnesota writer to compete in the Smallest Penis in Brooklyn pageant. The divorced, 50-something Van Dinkle lost by a (pubic) hair in the first-ever such pageant, which shocked the nation in 2013, and has since gone on to discuss small-penis-related subjects on podcasts and to pose for “clothed female, naked male” photo shoots in the Minneapolis area. He occasionally blogs at The Grouch Editor.

He was interviewed numerous times by various media and Internet sources such as Playboy, Cosmopolitan, Rolling Stone, Maxim, and many smaller-scale online entertainment publications. His participation in the Brooklyn Small-Penis Pageant (yes, it was a real thing, Google it) has brought about quite a bit of attention from celebrities including Kendra Wilkinson, Seth Meyers, Conan O’Brien and even Miley Cyrus. His small penis measures just under two inches flaccid and yet he is still not the man with the smallest penis.

small penis pageant

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Why did he participate in this pageant? According to his May 16, 2016, interview on he decided to participate simply due to curiosity. He wondered whether the event would be a body shaming event or one to encourage pride among men with smaller than normal penises. Also, because of how comedic the event sounded, and he’s a pretty chill dude.

The Interview

Question 1: In one of your previous interviews, you stated that you realized pretty early on that your penis was below average in size. As a child, how did that make you feel? Did it cause emotional discomfort? Did you talk to your parents or anyone else regarding the matter?

Rip Van Dinkle: “One of my earliest memories is pretty traumatic. My parents used to make home movies, and when I was just a tot they filmed me taking a bath. Then, at Christmas, with the house full of relatives, they would screen these movies for everyone. The relatives, including aunts, my sisters, and female cousins, all had a great laugh seeing me in the bathtub, my little noodle clearly visible and bobbing beneath and above the water. Extremely humiliating.

I have pubic hair now, of course, but otherwise, my penis hasn’t changed much in size since then, as you can confirm from the full-frontal pictures I sent you, and as pretty much the whole world can see on the Internet. As for talking to my parents or seeking counsel from anyone else … no, I never did that.”

Question 2: When did you lose your virginity? Please describe the situation.

Rip Van Dinkle: “That would have been in high school when I was out on a double-date with a buddy and two girls from a neighboring town. We drove out into the country, drank some illicit beer, and then wound up on the grass outside the car. I had brief penetration with the girl I was with, but I honestly don’t recall if I came or not. It was very much a “wham bam thank you ma’am” situation, and not particularly memorable. Probably especially unmemorable for the poor girl.”

Morgan: Was the girl a virgin as well?

Rip Van Dinkle: “Oh … that was so many years ago, I couldn’t possibly say. If I had to guess I’d say that she probably was.”

Question 3: How many women have you had sex with?

Rip Van Dinkle: “I stopped counting long ago, but I would estimate about 15.”

Question 4: Do you prefer vaginal or oral sex?

Rip Van Dinkle: “I love both, but I prefer vaginal because psychologically it’s ‘sealing the deal’ or ‘scoring’. You have successfully planted your seed in the girl. That’s a turn-on.”

Question 5: Do condoms impact your ability to maintain erection and cum?

Rip Van Dinkle: “I’ve almost always used condoms, but I can see where some men might prefer not to. I think it’s more a psychological thing than a physical thing. Wearing a condom reduces the possibility of impregnation (of course), and that can reduce the excitement. I don’t believe condoms have affected my ejaculation.”

Question 6: Are there any particular issues you have experienced due to your small penis?

Rip Van Dinkle: “To this day, I avoid situations where my flaccid dick might be seen in public, such as locker rooms. I know, I know, that sounds strange coming from a man who competed very publicly in small-penis pageants, but for some reason or other I don’t mind if women see it, but I try to avoid the potential mockery of other men.”

Question 7: How wide is your penis?

Rip Van Dinkle: “I wasn’t sure, so I had to get out a tape measure. Three inches in girth. I’m about 1.5 inches in length.”

Question 8: What advice would you give women who are currently in an intimate relationship with a man who has a small penis? Any tips to make the sexual interaction more enjoyable?

Rip Van Dinkle: “I would say that after you have been dating for awhile or are in a committed relationship, it’s OK to laugh about his little cock if he brings it up. But it’s probably unwise to say anything when you first discover his smallness – unless, of course, you don’t like him and are looking for a way to end the relationship. No woman has ever said to me, ‘Is it in yet?’ But I have been asked, ‘Is it still in?’ (My dick sometimes pops out during intercourse.) I think if you have a wee willie, like I do, it’s a bit easier to achieve penetration and stay inside her if you have sex doggie-style, inserting your penis between her spread buttocks.”

Question 9: What advice would you give men with small penises? What wisdom would you share? Any tricks to make sex more enjoyable and better satisfy women partners?

Rip Van Dinkle: “You must have a sense of humor about it. Otherwise, you can sit home, feel sorry for yourself, and masturbate to pictures of women on the Internet. Society isn’t likely to stop laughing at your small cock, so you might as well laugh, too. As for satisfying women in bed … listen to her verbal and nonverbal cues. Find out what she likes. There is always cunnilingus, and there are your fingers and tongue. You can also experiment with strap-ons, I suppose, although I never have.”

Question 10: Are you currently in a relationship or seeking a relationship?

Rip Van Dinkle: “I’m divorced and am not currently in a relationship. I am hoping to strike up a relationship with Morgan – just joking. (I think.)”

Morgan: “Lmfao! Sorry, John, but I’m recently divorced (2 weeks) and already taken. Plus I don’t like long beards.”

Rip Van Dinkle:I do own a razor, lol.”

Question 11: How does having a small penis affect your life?

Rip Van Dinkle: “It’s mostly a societal scarlet letter. It doesn’t affect me on a daily basis because no one knows what I have (or don’t have) under my pants. But TV shows, movies, books, articles, and people making jokes frequently remind you that a tiny cock is less than desirable. Psychologically, you can feel that you are a less-than-desirable sex partner for women. You are conditioned to feel that most women prefer big cocks. Hence the prevalence of porno like ‘big black cock’ Web sites.”

Question 12: What do you think is the biggest challenge relating to having a small penis?

Rip Van Dinkle: “You have to overcome the notion that a small dick is synonymous with being a small man. You still produce sperm, you can still reproduce, you can still make a woman happy in bed.”

Question 13: Do you have children?

Rip Van Dinkle: “If I did, it’s doubtful that I would participate in a small penis pageant.”

Question 14: Do you have any age-related sexual difficulties?

Rip Van Dinkle: “Oh, certainly. It’s more difficult to get aroused, maintain an erection, and ejaculate. When you do ejaculate, there is less sperm. It’s like Mother Nature is gradually castrating you. When I was younger, just about any woman would make me horny. Now, I tend to need more mental stimulation. I think that’s why I’m drawn now to things like SPH – small penis humiliation. I’d love to find a woman who is into sexually humiliating men but who also respects you as a person. Not easy to find in real life, although there are plenty of women who do that for pay on the Internet.”

Morgan: Actually John, you can find sadistic women on websites such as

Question 15: Have you ever gone to seek professional counseling regarding your sexual issues?

Rip Van Dinkle: “When I was getting divorced, we had marital counseling, but that focused less on sex than on relationship issues. I have never specifically sought counseling for sex issues. Do you think I should?”

Morgan: You seem like you’re functioning just fine. I only ask because my educational background is in psychology.

Question 16: How do you cope with these issues?

Rip Van Dinkle: “Sense of humor, sense of humor, sense of humor. Realize that owning a puny pecker is hardly the end of the world. You have lots of company. Also, some women actually prefer a small sex organ to a very large one, because (they say) it is less painful.”

Morgan: I can attest to that! Huge dicks can be painful during extra penetrating positions such as doggy style.

Question 17: Would you ever consider writing an autobiography?

Rip Van Dinkle: “I doubt it. Other than participating in the small penis pageants, I don’t think my story is all that newsworthy.”

Question 18: What’s next for you Rip Van Dinkle?

Rip Van Dinkle: “A cold shower and an afternoon spent masturbating about this interview. Just kidding! I’m hoping they will resurrect the penis pageant, because I’d love to compete again. Also, I’ve done a few CFNM (clothed female, naked male) photo shoots (and one video) and I would love to do more. Believe it or not, it can be a turn-on to have attractive women ogling and laughing at your exposed, small ‘manhood’. Better negative attention than no attention, I suppose.”

Question 19: Would you ever consider becoming a porn star?

Rip Van Dinkle:Funny you should ask. Nick, the winner of the first pageant, was approached by a porn company about doing a film, but he turned it down. I would consider doing a brief appearance, sort of as comic relief, but I doubt that I’d have the required skills/stamina/charisma to do it full time.”

Question 20: Are there any interesting or inspirational stories you would like to share?

Rip Van Dinkle:Hmmm … I’ll have to get back to you on that.”


small penis
Photo of Van Dinkle with models by Amy Minnick

1 Comment

  1. The Year in Dinkle - The Grouchy Editor

    January 26, 2018 at 4:07 pm

    […] You can read Marlena’s interview with Rip by clicking here. […]

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