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The ‘Dating Around’ Season 2 Exit Survey

Netflix’s upscale reality dating show is back and so are we, to talk about the season’s best matches, most cringeworthy moments, and the horrible human being that is True

Netflix/Ringer illustration

Five first dates, one second date. Netflix’s upscale dating show Dating Around has a simple premise, but being a fly on the wall for a handful of blind dates is anything but simple. There’s awkwardness, intimacy, and, sometimes, even a guy who might possibly be the devil (if you watched, you know who we’re talking about). After bingeing the show’s just-released second season, staffers at The Ringer stopped cringing and started divulging their thoughts.


1. Season 2 of Dating Around swaps New York City for New Orleans—what are your pros and cons of the move?

Andrew Gruttadaro: More romantic after-dinner walks on empty streets that make it seem like you’re the only two people in the world! You absolutely cannot do the salsa on a New York City street.

Alison Herman: The pros are, obviously, the tax breaks. New Orleans is also a naturally romantic city—all that humidity gives you dewy skin!

The cons are that New Orleans is an extremely small town. Ben got set up with someone who could well be his student! Deva knows her date’s art! Brandon has literally already dated one of his matches! In New Orleans there’s just not the same overwhelming and exhausting—but also exciting—feeling of sifting through an endless sea of fellow singles.

Katie Baker: The con was how it inspired that one dude to quote Tennessee Williams to Demi in the lamest possible way. (“That’s so random!” was her iconic response.) The pro was everything else! I liked the change of scenery, I loved the idea of some poor New Orleans University HR associate getting the strangest phone call of her life from a frantic professor, and more broadly I’m now really looking forward to whatever city comes next. Please be Salt Lake City, please be Salt Lake City …

Jomi Adeniran: The pros: no conversations about who is a “real New Yorker”; also, the fact you can have a street band accompany you to your date down Bourbon Street is an incredible flex. As for the cons, I wish it leaned into the New Orleans motif more! We got only one mention of Mardi Gras and one mention of beignets the entire season. Lean into it, let’s enjoy the Big Easy.

Alyssa Bereznak: Pros: romantic Creole architecture and the ability to legally carry a cocktail on the street between a restaurant and a bar. (I see you, Ben and Alex.) Cons: cheesy references to Bourbon Street’s infamy and using a bead necklace as an excuse to kiss someone. (I’m talking to you, Justin.)

2. What was your favorite episode?

Adeniran: Deva’s episode was the most interesting of the six. She was fun and her dates were fun as well, save for one (we’ll get to him later). While who she would pick became obvious as the episode drew to an end, Deva’s banter with Maria, Toure, and Rueben was definitely a highlight of this season.

Gruttadaro: Ben’s episode was everything I look for in this show: the strange euphoria derived from witnessing supremely awkward interactions, a student/teacher run-in, the chance to see a total nerd actually hack it on a date with a model, and most importantly, character development. Ben started the episode as a stuttering ball of nervous energy, but ended it with at least a shred of newfound confidence.

Herman: Deva’s was great for introducing bisexuality to the Dating Around canon. Ben’s was the best conversation fodder by far, though nobody that earnest should be put within 10 feet of a camera.

Bereznak: Deva’s episode! It was gratifying to see someone fluid as the central character of a reality TV dating show, and the sheer variety of her suitors made for great television. Deva won me over with her unwavering grace in pretty much every uncomfortable moment. Not only did she weather True’s exhausting, one-sided poly philosophizing with patience, but she also laughed off some very awkward banter with Rueben (I’m still trying to piece together the logic behind his “healthy” cocktail) and turned down Brooke in a way that was both firm and gentle. Plus, of all the second date winners, I liked Maria the funky art lady the most. Their chemistry in the car ride home had me squealing.

Baker: Deva’s. It just offered so much: that Ulla Johnson dress of hers! That guy’s “healthy drink” order at the bar that involved Jameson and Sprite! Artisanal eye masks! The worst human alive! A famous father! The words “crushed under the boot of capitalism” and the words “I live off rental income!” The beautiful crackle of actual chemistry the very instant that Deva’s and Maria’s eyes locked! Telling a dude he can feel free to browse your Instagram when he asks for your number! This was a good episode that I would recommend to someone who had never seen the show before.

All screenshots via Netflix

3. Your least favorite episode?

Gruttadaro: Actually, the premiere episode, “Justin.” The man himself was a cipher, which not only made it hard to guess which way he was leaning but also frequently halted conversation. And of all the girls, he picked the one who pulled the “[fake yawns] Wow, I’m really tired I should head home” move!

Bereznak: Ben’s nervous energy was just far too distracting for me to enjoy watching him do much of anything, let alone navigate the occasionally uncomfortable contours of a first date. It began with his bungling of a greeting/hug with Jaden and peaked at his declaration to call Stephanie a car because he felt uncomfortable with their student-teacher dynamic.

Herman: Heather’s dress was distractingly bad and her dates were neither magnetically sexy nor breathtakingly cringe. They were just normal, boring dates, and while I wish the best for everyone involved, the episode didn’t tell me anything I couldn’t observe in an average Midtown bar.

Baker: Probably Brandon’s, because several of the suitors felt like duds? That said, I really liked his decision to go on a second date with Justin even though he was about to move to Austin. It sort of felt like a win-win: If the second date was meh, they can wish each other happy trails and go on their merry ways. If it went great? Well, they need kindergarten teachers in Texas, don’t they?

Adeniran: Let me just get this out of the way first: I’m sure Ben is a great guy. He’s obviously very sweet and really nice. But watching him fumble his way around his blind dates was maybe the most cringeworthy piece of television I’ve seen since the “Scott’s Tots” episode of The Office. I mean, oh my God, it was rough. It was like watching George McFly in Back to the Future. I hated every single second of it.

4. Who was the best character in Season 2?

Adeniran: Deva! Her vibes were so welcoming and she got along with pretty much everyone. She was charming, funny, curious, and everything that makes a first date fun. I would watch an entire series of her dating. #MakeDevaTheNewBachlorette2020

Herman: I want Deva to adopt me. Runner-up: Justin’s date who freely talked about sweating and pooping. If he can’t handle your honesty he doesn’t deserve you, girl!

Gruttadaro: Ninety-nine percent of the time, Ben was all like:

But then 1 percent of the time he was like:

The depths!

Bereznak: From her very vocal love of animals to her Cabaret-act mannerisms, Heather seems like she’s three Instagram posts away from getting her own Bravo show.

Baker: In one corner we have the baby duck that slept in the crook of Heather’s neck and was then released into the wild where it was later shot down by Truman and his college buddies Coolidge and Buchanan. In the other corner we have the anesthesiologist’s hedgehog, Quill Smith. Tie goes to the punner.

5. Who was the most loathsome character?

Gruttadaro: I’m pretty sure everyone is going to say True here. Aside from his generally off-putting aura, he went from “I make a living on rental income” to “I only date bisexual women” to “I’m polyamorous but only I can date multiple people; my partners can’t.” Fahuuuuuckkkkkk that guy.

Baker: More like FALSE, am I right? Oh my god, was that guy ever a sentient fedora and a half. You know he went home and immediately logged on to the comments section of Roosh V’s blog to recap his night. The way the awfulness kept unfurling was breathtaking to witness. I really hope his kept-woman ex-girlfriend extracted a WHOLE LOT of that rental income during their time together.

Herman: “I only date bisexual women because being into women is really important to me” is obviously code for “I’m into group sex where I’m the only dude involved.” Good on True for confirming that hunch by being open about his polyamory; not good on True for literally everything else, including a total lack of self-awareness and that weird “suicidal vs. homicidal” comment.

Bereznak: True’s hatred for women began to peek through when he claimed his ex-wife wanted to be a “kept woman” and crescendoed at the moment he bluntly shot down Deva’s suggestion that his ideal vision of a poly relationship—one in which a man is the only one allowed to date other people—is unfair. Though he claims his attraction to women is a crucial element to who he is, he apparently has no interest in them beyond that. No thanks!

Adeniran: True is like if Future shaved his head, grew a beard, and started shopping at Men’s Wearhouse.

6. What was the most cringeworthy moment of the season?

Herman: Ben insisting he’d need to call HR before going on another date with a student at UNO, where he teaches. His heart’s in the right place, but judging by her body language, assuming she’d even want another date was pretty presumptuous!

Gruttadaro: Shout-out Deva being like “you should definitely find me on Instagram.” I hated to watch it, but respect the shit out of it.

Bereznak: Ben’s overly conciliatory goodbye to Stephanie made it seem as though he was infantilizing her and felt really condescending.

Adeniran: Of all the stuff that Ben did in his episode that made me go either “yikes,” “oh no,” or “please make it stop,” the conversation he had in the car with Jaden was so rough. To see anyone get turned down is hard, but then to see him react the way he did, honestly started to make me hyperventilate. Again, I’m sure Ben is great, but whose idea was it to put him on this show?

Baker: I saw Saving Private Ryan in the theater with my dad right when it came out, and as we were leaving the movie he announced, “That might have been the best movie I’ve ever seen, and I never want to see it again.” I thought about that capsule review the second Ben’s episode ended. It was one of the wildest rides I’ve ever been on—from the opening voice-overs about Ben being too good for this world to the closing scene of two be-sweatered, generous souls in a stilted embrace—but even the thought of seeing, like, a GIF from the episode causes my heart rate to spike. Luckily, scrolling Ben’s wholesome Twitter causes it to relax.

In your opinion, what would be the hardest thing about going on five dates at the same place?

Herman: Pretending I don’t feel gross wearing the same outfit five times for the sake of continuity.

Bereznak: Trying to match the excitement and delight of my date when they try the same specialty craft cocktail I’ve been sipping on for four nights in a row.

Baker: It just seems like so, SO much gnocchi. What do I look like, a mukbung YouTuber?!

Adeniran: You’d get sick of the food by Date 3, right? I don’t like eating the same cereal after three days. Plus, you’d have to stare at a menu and pretend like you don’t know what’s on it. The fun of a first date is discovering the menu together—it’s hard to do that when you’ve read the menu back and forth a few times already.

Gruttadaro: So you’re telling me I gotta wear the same outfit five times? How far apart are these dates? This seems like a lot of laundry.

8. Who made the worst choice?

Bereznak: Brandon. Justin was definitely the best dressed and the coolest. But he was also, due to his imminent move, categorically unavailable.

Adeniran: Brandon chose someone who outright told him that he would soon be leaving New Orleans. In the moment, that might not have been the worst decision, but with the world the way it is, I can’t imagine being in a long-distance relationship right now.

Herman: Brandon, who made the ultimate commitment-phobe move of picking the guy who is LITERALLY UNAVAILABLE BECAUSE HE’S ABOUT TO MOVE TO AUSTIN. Way to self-sabotage, dude! (I have no doubt he pursued other options, including my personal pick, Ronald, off-camera.)

Gruttadaro: Justin, Justin, Justin. Come closer. Just a bit more. OK, good: I … don’t think that girl liked you even a little bit.

Baker: Justin should have chosen Barbara! Great name, fun vibe, bold sleeves, didn’t bail on him the first instant she could the way Ann did. Also, while I loved that Ben chose Alex, who absolutely radiated serenity and kindness, I have to admit that I would have loved for him and Kat to get together, play FIFA, and talk about their breakups some more.

9. Which second-date couple actually has a shot at a long-term relationship?

Bereznak: I have yet to Google this, so I may be completely wrong, but Deva and Maria seemed great for each other in the long term. They’re both exceedingly stylish and creative and had a lot of common ground. Plus, all that chemistry. I ship it!

Gruttadaro: I really hope Deva and Maria ride their bikes into a neverending future, happily ever after.

Adeniran: Heather and Ernesto by far. They really seemed to connect on the date and frankly, they were the only couple I had real interest in after my binge. I hope they worked it out post-show and are enjoying a red-meat-free relationship together.

Herman: I’d bet money that Deva and her lady love have already U-Haul’d.

Baker: I’d love to imagine that somewhere out there, Zach and Demi are in the midst of a beautiful socially-distanced rom-com montage, doing salsa dancing via Zoom and standing on ladders 6 feet apart to install a new gutter system.