I Like It Anyway: Jen Kirkman and Millionaire Matchmaker
By
April 7, 2014


Illustration by Paige WeldonWith I LIKE IT ANYWAY, James Austin Johnson interviews a fellow comedian to discuss an activity or artifact that they love
so long as it’s uncool, unbecoming, or otherwise unacceptable.

Everybody was making out with each other for years by the time I realized that if I wanted to go on a date with somebody I could just ask. One moment there wasn’t a girl and then suddenly one presented herself as if from nowhere. I don’t think I ever actually ended up asking. Senior year of high school, arms locked, we were good, chaste Christian young people taking to the opera of an evening, just somehow. I was just as terrified to talk to her as I was of letting my hands go anywhere near her, but as calmly as she drifted into my company at school, she took my hand and messed with it in hers while the singers sang. There was no hanky-panky nohow, not unless you count the thrust and tickle of our athletic handholding and there still wasn’t for a long time after that. It was a safe first date, and lucky that because it could have been so much worse. I still don’t know what I’m doing.

First dates are high-wire acts. The complex selves we’ve grown and broken into are shoved into strange, new lights as we do our best to pull together a last-minute Cliff Notes of our lives. They’re almost too much to handle that early in a relationship, as Jen Kirkman (Drunk History, Chelsea Lately) related to me from a Bluetooth thing in her car. Jen’s been a favorite stand-up of mine for a while now. Her book I Can Barely Take Care of Myself is a bestseller, and not only does she record her own hilarious podcast called I Seem Fun, but her phone calls with Paul F. Tompkins frequently steal the show on his Pod F. Tompkast. And it’s pretty much everybody’s opinion that no one spins a better Drunk History yarn than Kirkman. But I also found out Jen’s an expert on first dates, having seen so many by watching every episode of Bravo’s Millionaire Matchmaker as it airs. There are few things more derided by highfalutin alt comedy types than reality TV and when someone as awesome as Jen Kirkman couldn’t give a shit what the cool kids think of her taste and rattles off her favorite Matchmaker moments, it makes for a very fun I Like It Anyway.

Jen, how’s it going?

It’s going good. How are you?

I’m pretty good. I’m just chilling in my bedroom getting ready to interview you. Is that cool?

That’s totally cool. I’m in my car.

Are you staying safe?

It’s Bluetooth through my speakers. I don’t even have to wear anything.

Well that’s good. I want to make sure that you’re obeying road law. So I heard you watch Millionaire Matchmaker the second it comes on?

Yeah. And I hate you for implying it sucks [laughs] because I think it’s one of the last reality shows–except for some of the little bits they do–that’s mostly real. I’m not embarrassed to say it. I do watch good stuff: Letterman, the Daily Show, Mad Men. I’m not an idiot. But it’s appointment television for me. If I’m home I watch Millionaire Matchmaker when it comes on. If I’m not at home it’s the first thing I go to on my DVR when I have time to watch things. I cannot get enough of it.

It’s great to find something that you really like. Even if you can’t necessarily explain why it’s good.

I can try to explain why I think it’s good if you want to hear. I’m sure Pat Stanger is a nice person and if I ever met her, I’d be totally star struck. So I hope I’m not saying anything mean about her. But I find it funny that she’s a second-generation matchmaker. I guess her mom and grandmother were both matchmakers, but she was adopted. Not that that means it can’t be learned by trade. But it’s not like it’s in her blood. I guess that’s irrelevant. But my thing is, she’s in her 50s and she’s living with a guy. Now the episodes, if they have extra time, are about her and her guy trying to work on their relationship. And her big thing is, “don’t move in with someone unless there’s a commitment.” And her guy asked her to move in with him and he only gave her a promise ring, which I feel like if you’re in your fifties is a little lame. She’s giving all this advice, but we’re not sure how well her love life is going.

I’m just fascinated with it. She really wants to fall in love. And I’m fascinated with watching people on first dates. And I’m fascinated by the very real “looks” thing, like how you have your type. One of my favorite things that she’ll say to someone is, “Who’s your celebrity crush?” Then she’ll try and find people that look like a real life version of that person. And then she’ll get other people that don’t. And the person will go right to the celebrity lookalike person. I’m just fascinated with people’s chemistry, how people pick people. I’ll get dramatic and play along, “Oh this guy doesn’t want the party girl he says, but he’s gonna pick her and the date’s gonna go terrible.” I love eavesdropping on people. I think it’s fascinating how quickly some people fall in love.

The elements of the show that must be appealing to you aren’t the cheesy reality show scenes they shoot later, but the actual emotions that show up. There’s humanity in it. It’s not all editing and dramatic music.

No, seeing people’s psychology is very interesting on it own. There was this one doctor who wanted to find love, and he eventually wanted marriage and kids. And he was willing to date women that were age appropriate for him, like women in their forties. But he could not calm down on the first date. [Stanger] was like, “Do not bring up marriage and kids on the first date.” And he was like, “I won’t!” And on his first date with this woman he’s like, “Do you want to get married and have kids?” And she was like, “Someday,” and he was like, “When? Would you want to do it soon, because we are getting older and that’s important to me.” It was crazy. He could not understand why that woman was offended and not enjoying herself on their date. He was like, “What? I have to find this stuff out.”

You can’t change people. I just love watching people like that, who never find a match and you’re like, “You’re never going to make it.” [laughs] And I also like when it seems so sweet for people too. They just drink champagne and eat strawberries and fly around in helicopters.

So are both of them on the dates millionaires?

No, the person looking for love is the millionaire. Say she’ll have Charlie, and he’s a millionaire and he’s looking for this kind of girl. She’ll interview like ten girls. Some of them might have a thing going on but none of them are usually millionaires themselves. Then she’ll have a mixer where she has drinks for an hour, and they’ll pick one person who he wants to go on a date with. She does have women millionaires on there too. But that always bums me out more.

What’s such a bummer about it?

For some reason the girls that want the dates that aren’t millionaires are always in college, maybe nursing school or they run their own hair salons. They’re never going to be wealthy, but they have careers or they’re striving for something. They’re never just a cocktail waitress or something. But usually when the guys are the ones that aren’t millionaires, I don’t think their life is going to get any better. A couple of them have been stand-up comics, people no one’s ever heard of. Or they’ll get a telemarketer, some job like that. And I think that in real life, this millionaire’s club that’s located in Los Angeles, I think is an escort service. Like, she has a rule about no sex before monogamy. She doesn’t want anyone in her club to have sex unless they’re in a committed relationship.

That mixed with the matchmaking element makes the whole process feel a little antiquated for Bravo.

It’s very antiquated, but the people involved in it are usually not. You can tell when they’re like, “Yeah, great. Two drinks maximum on a date, and no sex before monogamy. What date is this? You’re only going to have two drinks when you’re getting to know someone? No fucking way.” Whoever the millionaire is, man or woman, she makes the man plan the date. So when the woman is the millionaire, the man still has to plan the date.

Oh no. I don’t agree with that at all.

He doesn’t have the money! Sometimes the women get to take over. “Hey, I got this.”

“You wanna get some Subway and watch TV with my friend Jeff?”

That’s another thing that’s fascinating about it. Because sometimes you watch it and think maybe some of the old fashioned ways do work.

I was wondering if you had any sort of ritual when you watch it? Like, I really like New Girl. I like getting some white wine, maybe an edible and watching New Girl when it comes on. It’s weird. I’m a 24-year-old hetero male but that’s my thing.

See, now that’s something that you would tell on your match tape. [laughs] My ritual is usually, this sounds so sad that I do this one night a week but I’ll order in from this restaurant some salmon and asparagus. Maybe some wine, maybe not. I center my entire dinner around Millionaire Matchmaker. It’s the only show I watch where I’m not on my phone or laptop the whole time. Except for Mad Men.

That’s pretty cool. Mad Men and Millionaire Matchmaker.

But Mad Men‘s not a guilty pleasure.

No, you can feel good about liking Mad Men. Why isn’t it okay to like reality TV? Obviously it is very popular. I’m a comedian as well, and it seems like people who do something like that with all their time, it’s not cool to spend your off time with that stuff. Or at least if you do, it has to be buried under a million layers of irony.

I personally don’t think it has to be. I’m not embarrassed about it, and I don’t think that show is particularly bringing anything bad into the world. Like I haven’t seen Duck Dynasty, but I don’t enjoy hunting or guns, so I would feel like that’s not worth my time. But I guess [Millionaire Matchmaker] gets a bad rap because, especially if you are like a comedian, it’s like I should be only watching things that I can learn from all the time, smart things that you analyze and talk about the character development, blah blah blah. But I feel like [Millionaire Matchmaker] is not totally fake. You can get a lot out of real life. This is one of the only ones that’s not like Housewives where they’re simulating drama and throwing wine glasses and becoming caricatures of themselves. Because the characters only appear on each episode once, they’re not trying to be anything, they’re just honestly going on a date. And I just love it so much. It’s almost like a poker game if I enjoyed poker. You can kind of see what people’s tells are, their nervous tics, how they act on a date. It’s kind of informative in a way, and even I can recognize myself in the people on the date, like “I do things like that.” I’m just very interested in relationships, so that’s why I like it. And people say, [Stanger] is so annoying, but that’s also what I like about it.

She’s not annoying–she’s just from a more outspoken area. She really likes the f-word.

That’s the only fake part to me, sometimes she’s a caricature of herself. She’ll do a lot of things like, “Listen to me! If you don’t do this,” and she’ll point to something, “If you don’t buy her dinner, then you don’t get this,” and she’ll point to her vagina. And you’re like all right. I love hating that part too. In the age of the Bachelor–that show is so ridiculous–and [Millionaire Matchmaker] actually lets people talk. You can hear them having conversations. My favorite episode is when Patrick Swayze’s brother was getting set up with someone and he’s a deeply disturbed-seeming guy. Maybe they were just having fun with the editing. I guess he was with Patrick for the last months of his life. Every single question the girl asked he answered in a timeframe of taking care of Patrick. The girl’s like, “You love snowboarding, have you been snowboarding lately?” And he’s at dinner with her and answers, “Um, the last time I went snowboarding was the second to last week of Patrick’s life.” Everything was that. “Well, I haven’t seen a play since pretty much after Patrick died. He’s here on the date with me now. He watches over everything I do and say.” I mean, that’s completely real.

Yeah, it seems like there’s more of a struggle on the faces of the people on the show. The people on this show really want something to happen and when it doesn’t it seems like that where the drama comes from.

And also the drama can come from other things, there was this old man who wouldn’t go out with anyone over 40 and he’s in his 60s. And he goes out with this woman and he takes her out on his boat for the afternoon and she’s so not into it within like the first second. They’re stuck on a boat! And you can see on her face, “I know we have to get a couple hours of footage, but once this thing’s off I’m not going to the next part of the date.” And that’s exactly what happened. So I feel bad for the person, but I love watching the person who has no idea he’s being awful. The old guy goes back to Pat Stanger’s office and he’s like, “That woman was a cold bitch. Stop setting me up, I need young girls that are alive!” Lack of self-awareness.

It’s hard to be accurately self-aware at all with dating. Especially with first date nerves. Has anyone ever tried to set you up?

I think my friends don’t want to get involved. No, I don’t think that’s ever happened to me. I’ve gone out with people that my friends have known and done some recon with them. No one’s ever been like, this person would be good for you. I’ve met people and we’ll have mutual friends and I’m like, “Why didn’t you put us together before?” But no successful matches. People have mentioned it or shown me a picture or described someone and I’m like, “No, you’re completely way off.” Maybe I want it to happen though, it seems nice.

It seems nice to have some of the work taken out for you, but they’ve never worked out for me. That could just be me. I mean, all my most successful relationships have started with someone coming over to a dorm room to borrow a DVD. There’s no way to replicate that with Tinder or a matchmaker.

There’s something nice about just running into people. “Oh hello nice person I’m meeting, or friend I never looked at this way.” I had a friend who would have dinner parties for couples and then invite a few single people who she thought might like each other. But I don’t think I was ever invited to one. [laughs] I think at this point nobody’s even bothering with us. Nobody’s thinking about that anymore. I think my friends would think I would be insulted by that. Unless they’re like, “I’m best friends with James Franco, why don’t I hook you guys up?” As far as I know, no one is.

Everything’s so chilled out now. I don’t think you’re even supposed to go on dates anymore. I have no idea.

I think you still can. I still love dates. I like a proper date. But now I feel like a date happens the second or third time you hang out with someone. “Okay now we’ll have a proper date. I know we’ve met up drunkenly a few times since we met though.” Things just don’t come in the same order that they used to. I will say, I went on a real date once that was very uncomfortable. Like, “I don’t know you, let’s sit down and have dinner.” It just brings up a lot of weird expectations.

It does suddenly feel weightier now to do that. It’s already complicated enough having to watch someone you’re interested in eat for the first time. There should be a foundation of knowledge of each other before seeing each other eat. Eating is so–

You’re right! Why are we eating first? We should eat separately and get drinks at 9.

Eating’s disgusting. Unless you’re at home and watching Millionaire Matchmaker with nobody bothering you.

Exactly, just like me. That’s the best.

 

You can catch Jen performing stand-up comedy 4/19 in at North Door in Austin, TX, 4/25 at Local 506 in Chapel Hill, NC, and 4/26 at Zanies in Nashville, TN (and you should totally go if you’re nearby). Chicago residents would do well to see one of her two live tapings of I Seem Fun at the Hideout on 6/7 (and you should totally go to that too).

 

The Higgs Weldon is a humor website with funny stories, articles, cartoons, and one liners. It was started by the Los Angeles stand-up comedy community, but takes submissions from everybody. Please read and enjoy our jokes!


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