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Dear Michael Ian Black

In his excellent new book, You’re Not Doing It Right: Tales Of Marriage, Sex, Death, And Other Humiliations, actor/comedian/writer/podcaster Michael Ian Black offers a funny, startlingly honest appraisal of parenthood (Chapter 10: “I Hate My Baby”) and marriage, where he and his wife daydream about divorce. “One of the unexpected joys of being married is the hours of fantasizing it allows me to do about how much better my life would be if I got divorced,” Black writes in Chapter 12, “A Little Hard Work.” But You’re Not Doing It Right isn’t as bleak as that sounds; Black is a family man who loves his wife and children, even if he sometimes dreams about being away from all of them. And that’s why we trusted him for The A.V. Club’s annual Valentine’s Day reader Q&A: Anyone in a relationship who doesn’t admit to those kinds of fantasies isn’t being truthful. Considering how unflattering a portrait Black occasionally paints of himself in You’re Not Doing It Right, we trust his honesty. The book comes out in stores February 28.

My wife and I have three boys. The oldest is 3, and the youngest is due on Valentine’s Day. With all the stress and both of us working 50 hrs/wk, how do I bring the romance?

Serious answer: The thing that I think is the most important is taking moments to express your appreciation to your partner. A thank you or a quick kiss can go a long way toward affirming your relationship and commitment to each other. That’s not hard to do even when you’re juggling insane careers and three kids. The hard part is remembering to do it. The other thing you can do is give away some of your kids.

Hey Mike, do you think it’s possible to go through life without loving someone (excluding family) and still be happy?

I don’t see why a happy life necessitates a romantic relationship. Love of family and friends can be just as satisfying as spousal love. The question is: Are you single because you want to be, or do you find yourself seeking love and unable to find it? If it’s the former, great. You’re going to have a terrific, fulfilling life. If it’s the latter, you probably have BO.

Dear Michael,
How can you tell if a relationship is going to last? What are some signs?
Also, can I get a free copy of your book? I’ll do whatever you want as long as it does not involve me paying money. Thank you and congrats on all your success!

1. I honestly believe you can never tell if a relationship is going to last. In my own marriage, which is going on 14 years, I don’t think of it as “I’m going to be with this person forever.” Instead, I think of more like, “I’ll probably be with this person for the next six weeks. Then I’ll re-evaluate.” I can’t think any further into the future than that. Which is not to say that there aren’t moments when I’d like to kick her to the curb (and vice versa). But after enough time together, I’ve learned to trust that the hard times will be followed by good times. Signs of a healthy relationship include: dry mouth, soreness, head spins, heart palpitations, and death.

2. No.

Dear Michael,
Last night, I stayed up late conversing with my roommate. He confided in me that he is a 23-year-old virgin. I tried to explain to him that it really isn’t that big of a deal, but he would have none of it. This is something that he constantly worries about, and sees as a major roadblock in the way of him having a happy life. Since pep talks don’t seem to work, what would you recommend to snap my friend out of his funk?

I would suggest fucking him.

They say money can’t buy love. Do you think this is true?

I don’t know if money can buy love, but it can certainly buy the opportunity to try loving a lot more people. Women may find you attractive, but they will find you a lot more attractive if you have $100 million. That doesn’t mean they will actually fall in love with you, but they will be much more open to that possibility. If you’re a lady with money, you’ll just end up resenting your financially struggling beau. Also, money can buy so much awesome shit that it lessens the need for love.

Dear Michael,
After ending a relationship with an ex-girlfriend of a few months, we’ve decided to maintain a friendship beyond our previous intimacy. While I obviously enjoy her company and do find our friendship fulfilling, I’ve found it’s sometimes been difficult being “just friends,” and part of me thinks one day we will rekindle our once-budding romance even if it’s highly unlikely. Any tips for not going crazy in this sort of scenario?

One tip: Stop seeing her. Don’t be her friend. Don’t hang out. Don’t talk on the phone. If you ever want to get back with her, the only way to do it is to go cold turkey from each other. You don’t want to be that softie ex-boyfriend she calls when she has a bad date or just wants somebody to talk to. Fuck that. That’s why she has girlfriends and gay male friends. Be unavailable to her. If she misses you enough (and you miss her), you will rekindle.

Dear Michael,
I wish you were my life coach. Instead, just advise me—what snack shall I serve to a guy friend whom I’d like to be more than just a friend?

Any snack is a good snack when served on a warm plate of your tits.

Dear Michael,
I get dumped in most of my relationships, but invariably, after a few months, every single guy comes crawling back talking about what a mistake he made. Are these guys just looking for little naked fun, or is there just something about me that is better in retrospect than in reality?

Because I don’t know you, I do not know the answer to this question. A good way for me to find out would be for us to have a secret affair for a few months, I dump you, and then see how I feel.

This is unfortunately true for a lot of guys: They meet somebody great, start to have serious feelings about that person, and then get freaked out about it and back off. Then, a couple horny months later, they regret the decision. I’m sure it’s not you. Just hang in there. The right guy will come along. Or not. I don’t know.

Dear MIB,
My girlfriend broke up with me the weekend of your show in Baltimore, so you kinda have to answer this for me. I bought tickets to a play coming up that I know she’ll be at. I bought them partially because I’m creepy and partially because I wanted to see the play. Should I go? Or is this just too much? Are there rules for seeing your ex?

I don’t think it’s fair to arrange your life based on what your ex may or may not be doing. Go to the play. But I warn you: Most theater is terrible.

Dear Micheal [sic],
I just moved to a new city and I am having trouble getting busy. I know that if I wait long enough at a bar and lower my standards that EVENTUALLY some guy will put out… but I don’t know if that’s the bus I want to get on. I’m fairly decent looking and reasonably funny—the issue I have is that men really just want to be my friend. Seriously, they love hanging out with me, going to record shops, seeing movies—but none of them will PUT OUT. I’ve made some truly excellent friends in my new city, but honestly, how do I get them to see me as a woman?

Do what I used to do when I was young and single: Slip them a roofie, and when they wake up, be sitting on their face. If that doesn’t work, nothing will. It’s a good question, one that usually comes from the guy, not the girl. I don’t know the answer: I don’t think you want to just start sleeping with whoever will have you, if only because you’ll start to feel shitty about yourself in a pretty short time. This was certainly true for me when I was single. As much as I liked the idea of sleeping around, when I did it, I never really enjoyed myself aside from the thrill of getting somebody to be with me. The other thing you might want to try is making subtle gestures towards your crotch and whispering “That’s my pussy down there” to guys you find attractive.

Dear Michael,
I went to a club recently and danced with a girl who proceeded to take offense that I didn’t get a boner while she was dancing with me. I found her very attractive, but I’ve always considered poppin’ a strained vein against a stranger in public to be kind of rape-y, or even rude. Have I misread one of the many unspoken rules of manhood? Hopefully my dance partner’s expectations were unique to just her; otherwise I have a lot of religious and societal guilt to unlearn.

The fact that you can control where and when you get a hard-on is amazing to me. This is something I have not mastered, as evidenced by my last trip to the dentist’s office. That being said, you are way in the right on this one. Grinding your turgid cock against a stranger is super rape-y and probably prosecutable.

Dearest Michael,
When my wife is yelling for an abnormal amount of time at our dogs, is she really yelling at me?

Yes. Although she might also might also be yelling at the specific choices she made that put her in your life. It’s probably both.

Dear Mike, 
Can I call you Mike?
Of course I can.
So, Mike, I’m in a long distance open relationship. He won’t be back until June. The problem is, since he left, my libido has skyrocketed. I’m like a puppy out for a walk, but instead of wanting to pee on and sniff everything that looks good, I just wanna have sex with everything that looks good. (This is exclusive to good-looking men. I haven’t resorted to humping good-looking park benches.) And I kind of have. It’s been raining men, and I haven’t been using my umbrella. (The umbrella wasn’t a metaphor for condoms. I use those. I just meant I get laid a good amount.) My question to you is, how does one prepare themselves for a monogamous relationship after getting so much game? I know he’s better than all the rest—even so, I’m nervous about the future. 
Thanks in advance, Mike.

I guess I don’t understand the problem. If you’re in an open relationship, then he doesn’t care if you screw around, and you don’t care if he does. If you guys are having the conversation about monogamy in the future, then you need to have an honest conversation with yourself about whether or not his love is worth giving up all that mystery cock you’re getting. I would suggest that, while having sex with strangers can be exciting and fun, monogamy has its own, richer rewards. Those rewards express themselves over long stretches of time instead of in the immediacy of a casual hook-up. I don’t know that monogamy is right for everybody, but I think it’s right for most people. Maybe you’re not at a stage in your life when it’s right for you now. If that’s true, don’t commit to something you’re not prepared to see through.

For a couple of months now, I’ve been dating a guy I like who obviously likes me back. The problem is that he’s incredibly unreliable/unavailable. I can count the number of times we’ve hung out on two hands (okay, closer to one), and for each of those, there’s one or two times we’ve had plans when he’s canceled. We both have odd schedules, and dude’s always had a good reason, but I’m seriously wondering if it’s worth it to keep giving him second chances. Should I stick it out for a good dude, or is it time to let it die?

Let it die. It sounds like you’re looking for something he’s not willing/able to give you. If you guys ever get together, he is not going to change, and you are only going to grow more frustrated and resentful. People generally tell you what they want, and he is telling you loud and clear that he doesn’t want a relationship with you. Trust that he is telling the truth.

Dear Michael Ian Black,
Avid fan here. I’ve been in a relationship with my girlfriend for five years now and things have been great... except for one minor detail, of course. She hates you and your stand up—particularly your work in Stella. In fact, she ran into you after one of your performances and didn’t take the opportunity to get an autograph. I mean, if she didn’t want one for herself, she could have at least gotten one for me. *Sigh* What should I do?

I’m confused. Why was she at one of my performances if she “hates” me so much? Why didn’t she get my autograph when she knows how much it would mean to you? The only thing I can figure out is that she told you she was going to one of my shows, but was actually fucking your best friend. Good luck.

Dear Michael,
I need your help. My wife and children recently moved to another city—she received a job offer that was too good for her to pass up. Now I’m living alone with a house on the market, waiting until I can join my family.  You’ve certainly been on the road performing—how do you deal with the separation? And do you have any tricks to keep things spicy?

Separation is the worst. There’s no good way to deal with it, other than to get on the phone and do Skype and try to visit. The other thing you can do is develop a debilitating poker habit. Poker is a game that requires tremendous patience and solitude. If you live within a couple hours of a casino, whenever you are feeling lonely, you can just drive to the casino and give money to strangers. It might make you feel better. As for spicy: I don’t know. My wife and I keep things decidedly bland. Sometimes I do the dishes, and that seems to make her happy.

My wife and I have been married for over 10 years and have one child together. I was brought up in a home where the TV was always on, we walked to school, nearly a mile, and rode our bikes everywhere. My wife’s parents were much more protective and did not allow her to even drive until she was leaving for college. My style of parenting is to let our child grow up and discover things on her own, and I would be there to prevent injury, not pain. My wife thinks that her style of parenting shows that we love her and that we show an interest in everything she does. So I guess my question is: How do I convince my wife to hire a hooker so we can have a hot three-way?

Good question. I get this one a lot. First of all, I think the idea of hiring a pro is the way to go as opposed to asking one of the mommies in your kid’s daycare. The hooker will be more comfortable with the situation, and most importantly, will get the hell out when you guys are done. Best way to do this: On Valentine’s Day or her birthday, have the girl already there when she gets home. Say, “Surprise!” and then go to town. If she’s uncomfortable, just say, “Baby. you look tense. Denise here is going to give you a back rub.” The rest will take care of itself. Of course, if the hooker’s name isn’t Denise, this plan might not work.

Dr. Schwartz,
As I write this, my wife is nine months pregnant with our first baby. The common idea is that we will rarely have sex after we have a kid. How true is this? What can I expect as time passes? Did I make a huge mistake?

As far as sex goes, no you will not have sex for the first six months of your baby’s life. But don’t worry about it, because both of you will be too exhausted and miserable to even want sex. That’s the good news. The bad news is, yes, you just made a huge mistake.

What’s a surefire way to break the ice on a first date?

Best strategy for a first date is to ask her questions. Just keeping asking her questions about herself. Her life, her job, her friends, her taste in movies and music and everything. People mostly just want to talk about themselves, so let her do that. While she’s talking, pretend to listen, and at the end of the night, she will believe you to be an attentive and fascinating conversationalist because you will have spent the evening discussing the subject she is most interested in.

Dear Michael,
I wanted to ask for some help for a friend of mine. She is attending a speed-dating event at the public library. What should I do? Just kidding. She is supposed to bring her favorite or least favorite book to this event in order to make a first impression on her speed-dating partners. What book should she bring?

I understand that this is a set-up for me to promote my terrific new memoir, You’re Not Doing It Right, and that would certainly be a good choice, but I am too humble to do such a thing. Instead, I would suggest she pick something that she has actually read in the last six months that isn’t US Weekly. If the last thing she read is The Hunger Games, she should bring that. If it was Wuthering Heights, she should bring that. But if she’s worried about being judged for what she reads, then she’s an idiot. Basically what I’m saying is, your friend is an idiot.