Photo Illustration by Nick Wanserski

As longtime readers of The A.V. Club know, each year we pick someone we admire and force them to answer readers’ romantic inquiries. This year, that poor soul is Hannibal Buress, whose latest stand-up special, Hannibal Buress: Comedy Camisado, is currently streaming on Netflix. (He’ll also appear in the upcoming season of Broad City, which begins February 17 on Comedy Central.)

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Though Buress is neither married nor specifically known for his romantic prowess, the comedian still has a knack for dishing out sensible, helpful guidance when it comes to dating, sex, and how to romance that special someone. And despite Buress’ laissez-faire attitude toward love—something that should come as no surprise to anyone who’s seen his work—he provides plenty of good advice to almost all The A.V. Club readers struggling to find (or maintain) Cupid’s favor, save the one guy who wrote in with a bogus premise about jerking off and Olive Garden. So, lovers, sit down, strap in (or on), and kick off the week of Valentine’s Day with Hannibal Buress, this year’s A.V. Club love guru.


Confused On The East Coast asks:
I’ve been dating a girl for several years since college, and we’re getting into the age where people are starting to ask when we’re getting married. I have a blast with her, but it’s hard for me to imagine hanging up my sexual adventures so early.

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Additionally, while we have a great time in person and it’s hard to imagine a person who’s more compatible with me, I’m finding her less and less attractive. Is this just the usual cooling of passion in a relationship, or should I call it off?

Hannibal Buress: Yeah. You should probably call it off.

The A.V. Club: Why?

HB: It seems like you’re losing interest and you don’t want to waste either of your time. Time is finite. Parts of this country are probably going to fall into the ocean. So you don’t want to be spending your time with somebody you don’t really like. Cut her loose so she’ll stop wasting her prime years. Let her go do her thing.


Art V. asks:
My girlfriend and I have been together for a year and a half, and we’re looking into experimenting with a threeway. She’s curious to try getting with a girl, but we’re not sure whether to find a friend and risk making things awkward or go for someone anonymous via the internet. Can you give us any advice on how to find a third?

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HB: I’ve never used an app, but somebody tells me there’s an app called 3nder where you can find a third. Maybe ask a friend because if you make it awkward, who gives a fuck, you know? That’s what friends are for, to make things awkward. You can try out all of them. Have a friend and see if that works out. If it doesn’t, maybe that’s not even a friend that you want to do it with anyway. And then you find another friend. And maybe it’s that person. And even if does go well, you might not even want to repeat it with that person. Then try it with a stranger. This is a bunch of different ways. You could find somebody at your job. Just go for it.

AVC: The job proposition could be even more awkward than using a friend.

HB: Craigslist. You know, you could order something on FedEx. Ask the FedEx person if they know somebody. Do you want to get this done or do you want to just dillydally? Just bring it out, make it happen, and just do it, you know? It’s like Shia LaBeouf says: Just do it. DO IT!

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Animator In Love asks:
My fiancé is an actor and I am an animator, though I also work full time in a non-animator job and he does not. We had a fight a week ago and it culminated in him pointing out he’s been in five plays since we started dating and I haven’t had a chance to finish any short films. Is it wrong to be jealous of your significant other who is in another field than you being arguably more accomplished?

HB: It’s not wrong. But when you’re not creatively fulfilled, it’s easy to look around and find unhappiness. Especially if you’re not happy and you’re comparing yourself to other people and that’s the closest thing to you, then it’s easy to say, “Oh man I’m not doing what I want to do.” So instead of being jealous, use it as motivation to figure out how to take a step up at your job.

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Or do you suck as an animator? That’s worth looking into. Are you good and you just haven’t been getting opportunities? Ask your friends to be honest with you, if they like your work or not. There’s so many networks now that are putting out stuff. Goddamn Hulu, Amazon, Netflix, all the regular networks… If you don’t have a job then maybe it’s you. Maybe you need to broaden your horizons and animate porn.

To sum up: No, it’s not wrong to feel that way, it happens, but you should channel those feelings into stepping your shit up.


Charley asks:
What’s the appropriate length to try and make eye contact with a girl without making it look like you’re staring at her?

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HB: It depends. Generally, it should be a quick glance. If you stare for any longer than that, you’ve got to talk to her right away afterward. If not, you just seem creepy. That isn’t a bad thing, though. Sometimes I stare too long and then I’m like, well, I guess I’m just staring. And I just own it and I stare a lot and that’s what happens. But I think the unwritten rule is a quick glance. If she makes eye contact back and it’s the proper situation and setting, then you walk up and make a move right away. So that’s that. Or you could just be the creepy staring dude and live your life and who cares, man? We all die, so just look at people.


CB asks:
I’m a senior in high school who has liked the same guy for four years. Should I tell him or not? What are the implications? Should I forget it and move on with my life?

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HB: What are the implications? [Laughs.] What are the implications of this huge decision?

AVC: When you’re in high school it probably seems like a huge decision.

HB: No, it does. It does seem like that.

First of all, there are no implications. If you tell him that you’ve liked him for four years, he’s got the leg up. He’s probably going to try to fuck pretty soon after that. There’s no real implications. If he says yeah or if he likes you then you work from there. If he says no then it doesn’t matter. No implications except for your own ego. You’ve got to get over your ego and just go for it.

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AVC: Should CB cop to liking him for a long time or just be casual about it? What’s cooler?

HB: I think you play it casual for the initial contact, and then if it goes positively then further down the line you talk about liking the person for a long time. I don’t think that’s something you drop right away. But it depends on your style. If you want to just put all your cards out, so be it. Who the hell am I? I’m just a comedian doing this to promote a project.


Focused On Forgetting asks:
I’d been hooking up with a closeted football player at my small liberal arts college until about a month ago. It was a really secretive and confusing two-month thing. As an openly gay dude, I realized it wasn’t a healthy relationship for me, and told him to stop contacting me. The problem is, I still can’t stop thinking about him. Like a middle schooler, I find myself making snapchat stories in the hopes he’ll watch them, Instagram posts in the hope he’ll like them, and just generally wasting time wondering what could have been. I’m tempted to contact him again to restart things, but know that’s not in my best interest. So, what’s the best way to get over someone you know isn’t good for you, even if you’ve ended things on your own terms?

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HB: The best way to get over somebody you know isn’t good for you? Usually murder. You kill that person and it’s like, well, that’s not happening anymore.

You have to go cold turkey and say I’m not doing this anymore. You should probably stop following his social media. Yeah. Don’t follow that stuff. Get away from them. Probably don’t watch anything football-related to remind you. Don’t watch Friday Night Lights. Don’t watch any movies like The Program or Any Given Sunday. You just have to extract yourself from the situation and go like that. Or just go through with it!

I’m the worst advice-giver. Like, “You can try this or you can just do it.”


Christiane JPG asks:
Do you believe in seeking out relationships/love or just waiting for it to happen? Are you ever afraid you won’t be able to truly love anyone?

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HB: I guess it depends. Me, personally, I don’t really seek that out. I don’t seek out love or relationships just because my schedule is crazy. I already know who I love, but my schedule is very crazy right now.

I guess it just depends on what you want as a person. What stage you’re in in life. I think it’s good to go out and be open-minded and have fun and go from there, and try to find somebody that you enjoy spending time with in general, and try to build it. So no, I don’t ever worry if I’m going to love someone.

Sometimes I wonder, “Why am I spending time with this person?” I’m like, “I should not have done that.” But you’ve just got to take it as it goes, I guess, depending on your temperament. Some people are too sensitive for that, and want to take things seriously. But I fly by the seat of my pants or the cuffs of my shirt. I’m trying to make up a saying but it’s not really working.


37-Year-Old Virgin asks:
I am 37 and in a getting-started, not-quite-serious-but-could-be relationship with a guy I really like. But I’m still a virgin. I haven’t told him this yet because it’s embarrassing (I lost a lot of weight and thus feel better about myself.) How do I even bring it up? Or should I end it before it really begins?

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HB: Those are your only two options? Do you bring it up or do you end it? Are you trying to fuck or what? Get it done!

I don’t know. How do you bring it up? I don’t know. Play that one J. Cole song where he talks about losing his virginity. Just play that over and over. I forget the name of it. It’s one song where J. Cole, in detail, talks about losing his virginity. Just play that over and he’ll go, “Wow, you really like this song.” And then you can say, “Oh, I kind of just relate. I enjoy it. He’s a great storyteller.” Just play that and he’ll get the hint.

I don’t know. It depends. You want to do it? A 37-year-old virgin, depending on the dude, the first time, your pussy might get wrecked, you know? So be sure to lube up and just see! You might as well just see what his reaction is.

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That’s some special information. You got your own social experiment going on so you can fuckin’ tell lots of people one by one and blog all of their reactions and that’ll be interesting. I can see that moving around a lot on Tumblr. “I’m A Virgin And I Told 20 Different Guys And Here’s How They All Reacted.” You could really leverage this virginity of yours into something on BuzzFeed, probably.


Jangus Brownstone asks:
I feel that I have trouble meeting people due to fear of crowds and strangers wanting to talk to me. I want to find that special someone, but I’m not quite sure how, as dating apps and websites haven’t gotten me much closer to even finding just ‘’someone.” What should I do?

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HB: I don’t know, dude. If the apps aren’t working for you, and talking to people isn’t working for you, then it sounds like you’re shit outta luck. Go read a book. Go somewhere quiet. Go to a museum and be like, “Hey, this is crazy, right?” Try to strike up conversations, and fail, because it sounds like your attitude is negative. And I don’t know how to help you.

Apps are killing it right now. Dating apps are killing it. People are fucking constantly from them, and meeting each other. Join kickball, dude. I don’t know, man. There’s lots of activities that people do under the guise of trying to fuck strangers. Trivia night, anybody? Come on. There’s so much stuff. Where do you live? Look up stuff, and if there’s an activity, there’s a group of people doing that, and they go to a bar after they do it, and then they talk a little bit and some of them go fuck. So find a group with similar interests and then you go from there. It’s not that tough, dude. They outnumber us, man!


A Quiet Reserved English Kid asks:
I was in NYC recently and slept with a particularly loud person. Like “is-someone-gonna-think-I’m-hurting-her-and-am-I-gonna-get-arrested?” loud. For future reference: Is there any way to bring this up without hurting the other person’s feelings? I don’t want to mansplain how they don’t have to scream like a porno, and then have it turn out that they just really like screaming like a porno.

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HB: First of all, I hate that he said “mansplain.” [Laughs.] I really don’t like that he said “mansplain.” Just the fact that you said “mansplain” as a man makes me less inclined to try to help you out of your lame-ass situation.

Just do stuff until the neighbors come! Don’t worry about that. If she’s loud then just enjoy the loudness, man. You’re not even from this country, dude. It’s probably not even that loud. You’re just used to polite British sex. [Meekly.] “Oh, oh. So nice. Oh, that was great.” It’s probably not even that loud. It’s probably just the exchange rate and shit that makes it seem like it’s louder.

Just enjoy sex, enjoy that she’s making noise. Or do the thing where you’re acting dominant but you just cover her mouth a little bit. [Laughs.] I’ve actually done that one before. You just grab her mouth a little bit, like, “Shut up.” And you play it like that. But asking her to quiet down? Fuckin’ loser. Don’t do that. That’s stupid.


Patrick J asks:
I’ve been dating this girl for about six months now, and I have to say it’s mostly going spiffy. Over the holidays she invited me to stay at her parents house for the night, and around midnight I went into the kitchen to get some late night ginger ale, and on the couch was her dad jacking it to Skinemax. He quickly changed the channel and acted like he wasn’t totally slapping the old monument.

Anyway, her dad has been extremely nice to me ever since and even gave me multiple Olive Garden gift cards. Should I keep accepting these gifts or is that messed up?

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HB: This story sounds fake. It sounds super fake. Maybe these other ones are fake, but they sound like relatable situations, a lot of these. Maybe the 37-year-old virgin one is fake. No, that could be real. This one’s garbage. I call bullshit. A dude jacking it during the holidays in his living room? A father on the living room couch couldn’t keep it together, he had to jack it, and the way he keeps you quiet is Olive Garden gift certificates? Hey, fuck you and this garbage piece of writing that you put together. I don’t like it. This shit stinks. Yeah, like he was jacking it on the couch during the holidays to Skinemax. Not regular porn, but Cinemax, soft, no visual penetration porn. Get out of here. And do better.


Monogamy Is Overrated asks:
I’m currently in a long term relationship with someone, and it’s been over four years. We have this monogam-ish thing where if we’re out with friends partying or whatever and we find someone attractive, we don’t really hold back sexually if there’s chemistry. My question is: As a straight woman, are guys intimidated by that kind of agency I have if they find out I’m with someone but free to do what I want? I’ve seen a couple people weirded out by that and I’m confused.

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HB: I don’t know about intimidated, but I think guys like to feel like you’re theirs, even if it’s just for the night. Like a dude doesn’t want to be like, “Yeah, and then she’s going to go back to her boyfriend after I cum.” I think that’s more of the reason. But some dudes also are like, “Perfect. She doesn’t want anything from me but sex. This is great. I’m getting everything I wanted and I don’t have to feel like I’m ghosting her or something.” So, it depends on the dude.

But do you have to say that? Do you approach it like that? Can you repeat with the same stranger, or do you have to have new strangers all the time? A lot of different questions that I don’t know that I’ll never find out about you, but there’s some details to that situation that I don’t need to really know. Some guy’s probably like, “I don’t want to think about how some other dude hitting that on the regular, and now her vagina is more contoured for his than mine.” [Laughs.] And they get intimidated by that. But there are some guys that probably are like, “That’s great. Good. Some other dude can take her to watch The Revenant or whatever.” It depends on the dude.


Dezbot asks:
I’m an older woman who’s been single for a very long time. I’d like to date again, but have no luck with online dating sites. Do you have suggestions for where I should go to meet older men who don’t mind dating women their age, or will I die alone?

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HB: I don’t know what the fuck you’re asking me for. Sounds like you’ve got to either suck it up or become a cougar. Just get into it.

I don’t know what city you’re in, but if there’s a college campus, go to the college bar, learn some dances… Go on YouTube, go on World Star, learn some cool dances, and just be that old, corny-ass lady at the club and get you some young dick, and train it up.

I’m sure there are older guys that date women around their age, but I don’t know about it. That’s not part of my world, that’s not what I see in entertainment, so I got nothing for you on that.

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Online seems like the best way. Maybe a book club. You have to find some widowers. How about you look up older dudes whose wives died and then just kind of see if you look like any of their wives, and try to play on that and kind of get into that. You have to really get psychological and deep with this. It’s not the same as just going to a coffee shop or dressing up and going to a bar. If you want a man around your age, you have to really go for it. And you’ve got to be open to moving to another state. You can’t just stay in your area, your city. You got a good opportunity that pops up, you’ve got to just go for it. Because you’re too old, you know?

AVC: Life’s too short.

HB: You have to just do it. Life’s too short. Or just go younger. Get your groove back.

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