Do You Want to Have Anal Sex With Your Funny Friend?

by A Dude

Fuck, marry, kill: A girl who’s really pretty but not very funny or good at sex, a girl who’s really good at sex but not very pretty or funny, a girl who’s really funny but not very pretty or good at sex.

Basically, this is “Fuck, Marry, Kill,” with “Sexy, Funny, Pretty.” Huh. Here goes. Fuck: Girl who’s really good at the sex but not very pretty or funny. Marry: Girl who’s really funny but not very pretty or good at sex. Kill: A girl who’s really pretty but not very funny or good at sex. Weird that I chose to kill “pretty”? I like pretty! Not thrilled with this outcome, to be honest. I’d imagine I’d just end up cheating on my totally funny but not pretty or good-in-bed wife, unfortunately. That sounds terrible, but if you’re gonna marry someone, you definitely need at least two of the three, if not all three! (A more interesting question: which two would you choose in a marriage parter, if you could only get two? I’d go with “Funny” and “Pretty.” Eventually you’re gonna stop boning anyway, so I’d rather have a dime piece who makes me laugh.)

On male/female friendship: Do you think it’s possible for straight men and women to have a friendship where one doesn’t have SOME degree of sexual interest in the other? Because sometimes the guy friend secretly wants to make out with the girl friend, and the girl is kind of aware of/reliant upon that, and it’s just part of the dynamic, even if it they never act on it. And then sometimes vice versa — the girl secretly wants to make out with the guy, but it never happens and the dude kind of knows, and it’s just part of the friendship dynamic. And sometimes the who-wants-to-make-out-with-who dynamic shifts, see-saw-like, especially if it’s a years-long friendship. But yeah. Thoughts?

It’s POSSIBLE but it’s exceedingly rare. Taking quick stock of all my female friends, it’s generally the case that there’s a level of sexual attraction (that is at least latent, if not overt) that goes at least one way. In many cases, said sexual attraction has even been consummated in the form of a (usually drunken) make-out/grope/bone, after which point it was mutually agreed upon that simply being “friends” was a better fit. I HATE it when my guy friends have female “friends” they totally want to get with, but it’s never gonna happen, and the girl totally knows it and uses it as leverage to manipulate the guy. (Girls do this a LOT more than guys do this, because we are stupid and will generally do anything if there is the possibility of sex at the end of the tunnel.) In those cases, I usually advise my guy friend to cease all communication to see how she responds. Sometimes it works, sometimes it doesn’t. I guess I have a few girls I’m friends with who I don’t wanna bone and I’m pretty sure they don’t wanna bone me, but like I said, that’s rare. This is probably because, at least for me, the main reason I want to become “friends” with a girl in the first place is because I want to stick my weenie in her v-unit. I have enough real friends who don’t give me sex as is. They are called “dudes.”

Dear Dude,
My husband and I are long-time fans of a local (male) artist. About nine months ago, after an event, the artist and I struck up a conversation about a subject of mutual interest and exchanged email addresses. We have since corresponded every couple of weeks. Our correspondence is almost entirely related to our mutual interest; we don’t share a lot of personal stories and never talk about our private lives. We do tease each other some, but it is pretty bloodless, as far as flirting goes. My husband thinks it’s awesome that the artist and I have this email friendship thingie. I share many of our emails with my husband, and have never written anything to the artist I wouldn’t want my husband to see.

Recently the artist mentioned at the end of an email that he had just gotten a new tattoo. I asked what it was and he responded with a photograph. Thing is, he’s only wearing a towel in this photo. This is not a tattoo that requires towel-only exposure to admire! (To be fair, though, it helps.) There’s nothing untoward about the photo — it’s even sort of blurry, and only shows his upper body. Now I’ve spent enough time at the gym to know that dudes with good abs like to show their abs off, and the artist has very good abs. He’s also an artsy-fartsy bohemian type; I dunno, maybe he spends most of his private time in the nude and the towel was a concession to modesty? But, still: towel.

A last few possibly salient points: The artist is straight and has a long-term girlfriend; obviously he knows I’m married. I do have a crush on him, going back years, but have never said or done anything suggestive or inappropriate. I blush a lot at his events, though, so I expect my attraction is fairly obvious.

I don’t really know what to think about the photo. Do you have any insight into this?

This reminds me of that Seinfeld episode where George goes and gets a roll of film developed (side note: how weird is it that that was a thing that people used to do?) and ends up thinking that the girl who works there is into him because he gets sexy secret photos of her in his roll. So he ends up taking sexy photos of himself that he thinks she’ll see when he drops off his film the next time. Of course, like in every episode of “Seinfeld,” he was wrong and ends up looking like an idiot. I’m not saying you’re an idiot or anything, but I think this is just a case of some vain artist with nice abs doing something a vain artist with nice abs would do. (Though you never did say where the tattoo actually is, so it’s hard to gauge just how “crazy” it is that he’s shirtless.) All signs here point to this being no biggie. He was probably just trying to be “artsy” or something stupid. So carry on with your innocent, not-dangerous schoolgirl crush!

Do you prefer I wear lingerie to bed? I don’t mind doing that sometimes but I don’t want to do it every night. Problem? If this is the case, what would you reasonably prefer I wear instead?

I think most guys would agree with me when I say that lingerie is pretty overrated. I guess it’s nice on occasion, but honestly, we rarely end up appreciating it aesthetically, so who really cares? Real talk — we’re just trying to get to the titties. I’m not saying that you should be wearing granny panties to bed with any frequency, but I think, like, cute boy shorts or cotton briefs and a sexy tank top is “reasonable” (and comfortable!), and if you wear that to bed, you should call me because I totally would want to run up in ya.

Say there’s a dude you’ve hooked up with several times during a 10-year friendship but never dated, and you start noticing that you are a totally different “TYPE” than literally all of the ladies he’s dated during that time. Like, you have a lot of very much more conventionally attractive peers in this dude’s History. (Aka his girlfriends are typically-prettier you.) Does that mean a thing? Especially in the context of some drunken/seemingly earnest comments he has made to you about how you are his #1 favorite sex partner of all time? Does he love my brain??

I hope you don’t want it to mean a thing, because I don’t think it does. If you’ve only hooked up “several times” during a 10-year friendship, it’s probably just that he was drunk and wanted to throw it in something at the time, and you were the most available option. That doesn’t mean he didn’t enjoy it a lot (aka calling you his #1 favorite sex partner, which is a great compliment!), but I think that means he loves your v-unit, not your brain? If he’s generally dating chicks who are hotter than you, and he only sleeps with you when he’s wasted (and even then not that regularly), than I think the writing on the wall is pretty obvious.

If you want to do it in the butt, are you okay with there sometimes being poop involved? You have to know that’s a possibility. EH? Also, what percentage of guys, in your opinion, like/want anal sex?

Poop on the peen is my number one fear of anal sex. Which is why anal sex, to me, has always seemed like a better “planned” activity, rather than a spontaneous one. (Aka, the girl has poo’d in the recent past, showered after, etc.) I don’t ever want poop on my peen, and honestly, if it were to happen, I don’t like anal sex enough that I would keep doing it in the future. Poo in the bedroom kinda seems like a dealbreaker. (Not a dealbreaker in that you’d dump a girl were it to happen, but a dealbreaker for the activity that resulted in poop on the peen.) I think some guys like anal sex on occasion or in the right context (aka you really wanna get all alpha male), but most don’t want it with any regularity. A bum certainly doesn’t feel better than a warm, squishy, v-unit. I’d say that maybe like 30 percent are into it? I know a couple of guys who REALLY love it, but they have some issues that aren’t pertinent to our discussion here. (I hope you don’t meet them, for your sake.) Randomly, I was at a party last night and was discussing anal sex with a bunch of girls, and they estimated that 4% of their female friends actually enjoyed it. Which seems way lower than what Cosmo or whatever would have you believe.

QUICK — when was the last time you masturbated?

Last night, at like 5:15 a.m. I was pretty intoxicated. I couldn’t find a towel or any Kleenex, so I cleaned up using some Christmas-themed tissue paper that a sweater had come wrapped in. Festive!

Previously: Do You Mind That We’re Hairy Sluts?

A Dude is one of several rotating dudes who know everything. Do you have any questions for A Dude?