If you’re anything like us, you binged all six episodes of Dating Around, Netflix’s new reality dating series, in one sitting. The premise is simple: One person goes on five blind dates and selects one person for a repeat encounter. Each episode unfolds in a compelling, often cringe-inducing way that, as Alison Herman wrote, “turns dating into a spectator sport, and a highly entertaining one at that.” We polled the numerous Dating Around enthusiasts at The Ringer on their favorite episodes, least favorite characters, most memorable moments, and where the show ranks in their reality-dating pantheon. All hail Leonard!
What is your primary takeaway after watching the series?
Matt James: Dating Around is captivating because of the lack of reality-TV confessionals. Without being told what the participants are thinking, we’re forced to pay closer attention to all the small moments. I found myself zeroing in on body language and tonal inflections for clues. If you’re a fan of whodunits, you might be just as interested in this whogonnadoit.
Kaya McMullen: Low-stakes dating shows can still be interesting! Just because no one is getting married at the end of the episode doesn’t mean I can’t be invested. The production value really made the show.
Nicole Bae: I’ve never gone on a blind date, and now I never will.
Katie Baker: Don’t tell jokes.
Alyssa Bereznak: Being a human being is just humiliating.
Rodger Sherman: Every waiter/bartender/ice cream truck operator who served the Dating Around contestants showed tremendous restraint by not saying, “Hey, that’s not what you ordered the last four nights on your other four dates with four other people! Same shirt, though.”
Noah Malale: My primary takeaway from watching the episodes is that I’m going to do everything in my power to ensure my fiancée never leaves me.
Donnie Kwak: Falling in like/love/lust is great fun.
Which episode was your favorite and why?
[Episode 1: “Luke”; Episode 2: “Gurki”; Episode 3: “Lex”; Episode 4: “Leonard”; Episode 5: “Sarah”; Episode 6: “Mila”]
Andrew Gruttadaro: I liked three episodes for three different reasons:
- Lex’s, because Lex was dope and hilariously dry. I’m pretty sure he almost made that dude cry when he made fun of his unibrow.
- Leonard’s, because it was just enjoyable watching old people complain about real estate and struggle with iPhones.
- Mila’s, because I was just so confounded by Jarry ordering a Bloody Mary during dinner.
Juliet Litman: Leonard’s episode was a true delight. Dating shows mostly rely on people too young to know that a reality program is unlikely to yield lasting love, and as a result they traffic in clichéd notions about relationships. Leonard’s episode was revelatory because he and the five women approached their encounters with an understated directness that would fail to register on The Bachelor.
McMullen: Gurki’s episode was the best, mostly because conflict makes for good TV. Also, despite the water leaking from the outdoor roof, her date restaurant was my favorite. Love a casual ambiance and a mason jar cocktail.
Bereznak: L E O N A R D! Not only is he a courteous, curious private investigator who praises the mental benefits of psychedelics, but he’s also a big ol’ romantic who wants a second chance at love. Plus: He owns significant “square footage” in NoHo, as his date Lauren (“I have three ex-husbands”) put it. Who cares if he tells weird frog jokes? Septuagenarian ladies of New York, lock it down!
On a more general note, I’ve watched a fair amount of reality TV, and this is the first time I’ve seen an older man date a woman who is also his age. I was so charmed by how interested he was to get to know each and every one of them, even Eileen, the weirdo artist who drew some squiggles on a napkin with her lip gloss. Props to Netflix for seeking a subject like Lenny and treating him and his dates with dignity and respect.
(As an aside, I would also like to note that the only people in this series who interrupted their dinner to look at their phones were his dates. A recent Nielsen study—and my own personal experiences—proves that millennials aren’t usually the rude ones with their phones out, their parents are. So there.)
James: Leonard’s. It turns out that blind dates are particularly interesting when the two participants show up to the table having lived entire lives already. The longer your life story, the harder it is to find someone who can relate to your experiences. How can we be loved if we’re not first understood?
Bae: Leonard’s episode was the only one in which I felt torn between two of the dates (Eileen and Dianna, of course), so at the end I was anxiously waiting to see who that extra coffee was for.
Baker: Lex! As a viewer I just really enjoyed looking in on a dating scene that exists outside of my own experience, and I loved seeing a “main character” like Lex who was a little bit of a tough nut to crack without being, like, a gratuitous asshole. Even the “weird” dates in the episode were charming. Queera Wang is perfect. And the episode even made me gasp a little: I was totally expecting to see Brad walk out of that crowd at the end! (No disrespect to Cory, my brother not only in Internet stalking but also in awkwardly telling people about it.)
Molly McHugh: Leonard’s episode was my favorite because I really liked the woman he chose for a second date and also: old people finding love.
Kate Knibbs: I mean, I have two eyes and a heart—Leonard’s.
Kwak: I watched every episode twice and Leonard’s held up the best. (I love his listening face, and date for date, his candidates were the most interesting.) However, don’t sleep on Sarah’s episode—she kept it entertaining.
Which episode was your least favorite and why?
Gruttadaro: I stopped watching Sarah’s episode at the 2:45 mark, which was the moment when she followed up “Shut the front door” with “What the Franklin Delano?”
McMullen: Sarah’s episode. I found her to be the least likable out of all the main subjects, so that’s probably why. She had really poor chemistry with almost all of her dates and took herself a little too seriously, which made it hard to watch.
Bae: I was so uncomfortable during Sarah’s episode ... but it’s also the episode that I can’t stop thinking about and recommending to my friends.
Sherman: I can’t imagine how the producers of this show decided to make Dull Handsome Luke the first episode. I guess they figured it was easiest to draw people in with the show’s lone straight white guy, but I wonder how many people decided not to power through and binge because of how little he brought to the table.
Litman: Luke’s episode is the most unremarkable—but that’s also why it’s valuable. Of all the six daters, he most closely resembles a blank canvas. He’s a generic type of guy that everyone knows or encountered in their 20s, and that’s why he was a perfect choice to kick off the show. Because he was an archetype, the clever editing and simple premise were on display.
Knibbs: I almost turned it off after the first episode. Luke was sweet but dreadfully boring, and he didn’t have chemistry with anyone, so it was a bit of a drag. Plus: Tiffany, the lip-smacking Jersey girl, deserves to be in prison for her crimes against eating in public.
McHugh: The first episode, because the dude was boring and the story that the woman he chose told about developing a “12 pack” was horrible, and perhaps mostly because I didn’t know what I was in for when I turned the show on and was unprepared for how uncomfortable it made me.
Bereznak: I wanted to rip my skin off while watching Luke’s episode. Like so many men who have vaguely lucrative finance and/or real estate jobs in the city, the man clearly thinks moving from Florida to New York is a personality. Because he rarely ever says anything of substance, the onus is put on his dates to either pretend like he’s doing a good job or lead the conversation entirely. Some women were more willing to take the reins than others. Victoria laughed uncomfortably and slipped into a goofy “I’m undateable” bit to fill the silence, and ended up getting that second date. Personally I related most to Ashley, who—after figuring out Luke was not interesting—tried to find out if he was, at the very least, fun. (“So do you go dancing a lot?”) I respect that she left the second she realized he was neither. I also hated the way he gave that speech to Betty, the Colombian divorcée, about how he was surprised that she was both hot AND deep. It seemed to me that this was all part of a strategy to go home with her. Based on how their car ride ended, it worked.
Baker: I’ve definitely included the disclaimer “the first episode is the least interesting” when I’ve recommended the show to friends. It just felt kind of like … every Tinder drinks date I’ve ever eavesdropped on? Which is fine! The show will lose something in the future if every episode tries too hard to be quirky. But I’m in no hurry to re-watch Tiffany lip-smack, is all.
James: Luke’s episode was by far my least favorite. Luke is like if Patrick Bateman from American Psycho had less personality (and hopefully less of an inclination to murder people). He’s a tall, handsome, blank slate of a man. Luke can talk for minutes at a time without actually saying anything. I was not surprised to see him pick Victoria, who has a surplus of personality.
Kwak: Like all of us, Ashley checked out very early from Episode 1:
Who was the most appealing character?
Baker: Episode 1’s Ashley had great style, great insights (“You’re such a real estate guy”), and the great sense to go ahead and call herself a Lyft.
Bereznak: Aside from Lenny, New York’s most eligible septuagenarian widower, I really appreciated everything about Gurki. First off, I would definitely read a blog about her skincare/workout/shopping routine because she’s an aspirationally hot and fashionable 36-year-old. But more important, she has a really compelling, complicated history that I am almost positive she has spent time parsing in therapy. The way she was so upfront and honest about her divorce was really impressive, and despite everything she’s been through, she made herself vulnerable. I knew I liked her the moment Justin was talking shit about his ex-girlfriend’s cat and she called him out: “Wait, so you made her get rid of her cat, and then you broke up with her?” Good for her for choosing a SoHo shopping trip in lieu of a second date with all of those meh suitors.
Knibbs: Leonard deserves happiness and someone to laugh at his bad frog jokes.
James: Leonard is easy to root for because he’s a very sweet, open person who’s already led a life filled with love. He was honest with the women he didn’t connect with and was careful to get Dianna’s coffee order correct at the end of the episode.
Bae: Leonard, the P.I. He was so sweet and was a patient date to the ladies he didn’t seem to vibe with. He even planned to set Lauren up with one of his sexiest friends once the two of them figured out they aren’t a good match. What a guy. (Lex is a fan, too.)
Gruttadaro: Maybe it’s just me, but I feel like I could listen to an old Jewish man reminisce about his LSD days for hours. Also, look at the face Leonard makes when you call him a pussy!
McHugh: Lex.
Kwak: The Twitterverse seemed to be as taken as I was with Lex’s confident cool, but upon second viewing his charm started to feel more like smarm. Meanwhile, Episode 5’s Sarah seemed to be universally disdained, but when I rewatched her episode I realized she’s operating from the same playbook as Lex: using wit as a defensive weapon. It’s just that her wit hasn’t been honed to a sharp point yet. If she remains single and dates around for about 10 more years, she’ll up her game and eventually evolve into Lex.
Litman: Mila seems like the world’s most agreeable person, narrowly edging out Lex for the crown. She was generous in conversation, decisive in who interested her, and even-keeled throughout. She is also luminescent.
Sherman: With apologies to The Bachelor, Brad is by far the most interesting Guy Who Briefly Appeared On An NFL Team’s Roster currently appearing on a reality dating show.
Who was the most loathsome character?
Bae: JUSTIN.
Bereznak: Gurki’s date Justin. The man’s dream job would be to play guitar on a stage every night, and yet he does not play the guitar. He voluntarily says the phrase “rosé all day.” He hates cats?? (See girlfriend anecdote above.) And most notably, he seems deeply unsympathetic to anyone outside his own limited life experience as a privileged white dude in New York. The way he bullied Gurki, and yelled “YOU LIED TO A MAN”— as if that’s some crime punishable by death—was just vile. He clearly has anger issues that, if I had to guess, are rooted in his own insecurities and trust issues.
In general, I felt like the straight men they found for lead women in this series were significantly worse than everyone else. But maybe that just says something about New York’s dating pool?
Baker: Justin sucked, but he led to a great interview, so thanks Justin!
Knibbs: From a moral standpoint, 100,000 percent Justin, who was straight-up disrespectful to poor Gurki. That guy sucked. However, I will say that Tiffany, the Jersey girl who loved to chew really loud, holds a special place on my Enemies List for being absolutely disgusting. Chew quietly, bitch!
James: Justin had a strong showing as the angriest, most judgmental white bro of the entire series. It’s one thing to lack the empathy to try to understand the societal pressures of another culture, but it’s next level to yell at someone when you can’t relate to them. Gurki had the strength to assume some degree of responsibility for disappointing outcomes in her past; Justin, however, will live his whole life believing he’s never been wrong or made a mistake. Good luck yelling at women on first dates, dude.
McHugh: In Gurki’s episode, Justin, who I refer to as Macklemore Haircut, used the phrase “so this is like an Indian thing” and also dressed her down for getting divorced with the phrase “you lied to a man ... as long as you admit that.” I can say with confidence that Macklemore Haircut has said the phrase “not all men” in his lifetime. In second place is Sarah, for many reasons but also because she said “kick rocks” too many times. (One time is too many times, honestly.)
McMullen: Justin!! What kind of person attacks someone for getting a divorce? Especially on a first date! The guy clearly has some unresolved issues with divorce and I would advise that he work those out before dating again in the future.
Gruttadaro: Jonathan, the dude with the Rollie Fingers mustache and sequin jacket from Lex’s episode. Why did he write a song containing the lyrics “I see Versace jeans across my wet dreams?” Why did he then read those lyrics out loud? Why does he not know how to use a fork?
Sherman: Episode 5’s John—sorry, Mr. John, his cool nickname. He’s the strip-club employee who bombarded Sarah with about 1,372 unnecessary sex jokes (such as insinuating Sarah’s choice in salad size may reflect her penis preferences), saw them fail, and decided to launch forward with no. 1,373 (attempting to connect singing with blowjobs).
Kwak: Honestly Mr. John seemed like he’d be a fun hang, but still: time and place, bro.
What was the most memorable moment?
Bereznak: I burst out laughing when “Mr. John”—the guy who works at a strip club and wore a deeply unbuttoned shirt covered in red roses—told us about his favorite drink: “White wine will get me hyped up, two, three glasses of wine.” Same dude. Same.
Also Lex’s date with Jonathan (the mustachioed guy in the glittery jacket) was really hard to watch. His song lyrics were mortifyingly bad. His story about sleeping with a guy who wanted him to also walk his dog was confusing and sad. And his table manners were agonizing.
Knibbs: In the Lex episode, Jonathan reads him what can only be described as light erotic verse while they’re at drinks, and the look on his face as he sits there—trying to arrange his expression so it remains polite but unable to hide his visceral distaste for such a profoundly awful poem—is the greatest distillation of the awkwardness of courtship I have seen recently.
McHugh: Brad, the Moviefone guy, was cute and lovable!
Baker: Leonard taking an extremely long time to grok “tight seal” and Episode 6’s Ashley correcting Mila that the teacher she once crushed on was a “her,” a very sweet “the surgeon is the boy’s mother!” moment.
James: The connection that Leonard and Dianna have while reminiscing about sex, drugs, and rock ’n’ roll feels like the most significant shared ground between any couple in the series.
Kwak: When Leonard wished Dianna a happy birthday in sign language, I caught a lump in my throat. Also, I think Antonio spoke for the viewing audience when he gave Sarah a three-pun limit early on in their date.
Bae: Antonio leaving the date after Sarah repeatedly told him how cute she found him. Woof.
McMullen: Gurki saying, “What’s happening right now is a culture clash.” I was in awe of Gurki’s calmness in this moment and also the fact Justin plowed right on ahead with calling her a liar. The guy does not know when to back down.
Litman: I am fiending to know about Leonard’s 1,900-square-foot apartment in Nolita that he had recently listed. That kind of size, in that area, is worth several million dollars. I’d be willing to pay even to see the floor plan. It has to be a rare, older building. I need to know more.
Sherman: Every single time we see the right person emerge from a crowd of New Yorkers. (The cinematography on this show was beautiful, movie-quality stuff way beyond anything I’ve ever seen on reality TV. There were about four times that they showed a street I’ve walked down before and I thought, “How the hell did they make that street look so pretty?”)
Gruttadaro: “I started a beverage company.”
What was the most cringeworthy line?
Bereznak: When Mr. John found a way to sexualize the “big salad” he was sharing with Sarah.
Baker: Gloria … ol’ buddy ol’ pal … on your next first date, maybe don’t mention the part about cheating on your invalid husband? If you feel like you’re about to spill the beans, just text your daughter some more.
Sherman: Do Tiffany’s mouth noises count as “lines?”
James: “Getting in shape is cool, yeah.” —Luke
Kwak: Adrian telling Sarah she was one of the most beautiful and interesting people he had ever met—like 10 minutes into their date. Also, Luke employing the tired-ass “How are you still single?” question to multiple women.
Who made the worst decision for their second date?
McMullen: I think everyone chose wisely!
Litman: I support all six decisions, and it’s not hard to feel this way. The stakes are delightfully low, so why not give that person a second chance? The biggest surprise was Lex picking Cory over Brad, he of the NFL and man-bun fame.
James: I don’t think anyone made a bad decision for their second date (including Gurki picking no one), but I was surprised at Lex’s choice. I guess Brad’s dominance in the bedroom really was a deal breaker for Lex because he otherwise seemed to really like Brad.
Sherman: JUSTICE FOR MAN BUN BRAD.
Bereznak: Sarah! I felt like she had real chemistry with Nick and that the startup dude she chose was too muted and boring for her. I get the impression she’s overcorrecting a little, based on her last bad relationship.
McHugh: Luke.
Kwak: Manny from Episode 2 deserved a second chance from Gurki. He didn’t take himself too seriously, seems like a responsible father, and he knows Krav Maga.
Gruttadaro: Personally I thought it was rude that Gurki chose shopping at Vera Bradley over any human being; and that she forced Netflix to hire multiple extras to gawk at her as she walked through SoHo.
Which couple do you think has the highest probability of surviving long-term?
Bae: Sarah and Matt. See: their shared fascination with robotics, mutual love for hydration, eating mad onions on their first date, and their earnest cab talk. Matt was not only the right choice out of the five dates, but he also seems like a really good guy.
McHugh: I want it to be Leonard and Dianna. Rooting for those two.
Gruttadaro: I’m really rooting for Mila and Charlotte.
Bereznak: Just based on what Mila told us about her propensity for monogamy, I think she and Charlotte have a good year or two in them. I could also see Luke and Victoria getting married, having two kids, and divorcing. But not in a good way.
McMullen: Mila and Charlotte—they had the second-date, flirty banter that you need and seemed genuinely excited to see each other.
Sherman: I regret to inform you the answer is None Of Them. (Look, this show is an extremely realistic depiction of NYC dating.)
If you could pick one of the dates to have his/her own episode as the main subject for Season 2, who would it be?
Bereznak: Brad, the former pro football player from Wisconsin. Honestly ABC should make him its first gay Bachelor. He’s got the man bun, he’s got the Midwestern charm. It could be really good.
Baker: Eileen! I was surprised when Leonard didn’t choose her. They seemed quirky and cute. But imagine an episode with her sampling from a cornucopia of Leonards! And I like the cut of Eileen’s jib: A few years ago, she got busted for illegally subletting her rent-controlled apartment on Airbnb and lost the case after failing to turn over various documentation “because she was ‘in the Hamptons,’ according to the landlord.” In related news: Now that I’ve seen Nick’s post on the subreddit “Brogress,” I’m extremely interested in having Nick as the main subject for a future show titled “Brogress.”
Sherman: Victoria seemed infinitely cooler than Dull Handsome Luke.
McMullen: Give me more Jarry! Mostly because I love a good accent. Also it would be interesting to have a bisexual main subject and have a mix of male and female dates.
Kwak: I’d be interested to see Antonio the firefighter weed through five dates—he seems sincere and no-nonsense. I also appreciated the Queens accent.
If you were asked to participate in the show, would you rather be the main subject or one of the dates?
Baker: Just reading this question is giving me anxiety.
Gruttadaro: LOL never. My lack of conversation skills is for privileged eyes only.
Knibbs: I really wouldn’t be either since I’m married and I love my husband. (And I love him even more since Dating Around showed me just how bleak it is out there.) But if I was single, I’d rather be one of the dates, because the experience would be shorter. This seems like absolute hell.
Sherman: I’m not sure I could handle five consecutive nights of happy hour drinks followed by dinners out followed by nightcaps at a third bar. I have work in the morning!
McHugh: One of the dates, because if you’re the main subject … I mean, are you wearing the same outfit to the same restaurants and bars multiple nights in a row, or are you just like … sitting there for hours as new dates filter in? Either way, that sounds weird and sort of boring.
Litman: I’d absolutely rather be one of the dates. The end product would provide an insight into dating and a person who you can’t access otherwise. I’d be presented with data points to analyze my own experience.
McMullen: I’d much rather be one of the dates! Mostly because I could not imagine going on the exact same date five nights in a row while still maintaining the same level of enthusiasm. Also I could not stand the awkwardness of one of those post-date Uber rides more than once.
Malale: This is a no-brainer—I’d rather be one of the dates. Being the lead requires coping with at least one bad date, and at least one borderline offensive encounter. And besides, the stress that must go into choosing one outfit that you must wear to all five dates is overwhelming. I wear a variation of the same outfit every night out as is, but knowing I have the option to mix it up is important.
Kwak: Probably the main subject, but pondering this did leave me with a question: Was there any pattern linking the actual real-life sequence of dates to who eventually got picked? Like, I’m curious if the second-date winners tended to be early in the process or later, or if it all ended up being completely random.
Bereznak: When I was younger my dad was dead set on teaching me how to golf, so he hired this instructor at the driving range to videotape my swing and play it back to me in slow motion. It was helpful for improving, but also morifying to see myself constantly flailing, and fucking so many things up at once. That’s how I imagine watching yourself as a lead on this show to be. But I guess if I were going to open up my personal life to the world, I would want to do it in a way that taught me something about myself too.
What is your favorite reality dating show of all time, and where does this rank in that list?
Gruttadaro: Hmm, Next? Room Raiders? Date My Mom? Dating Around doesn’t really touch those classics, but I do appreciate the emotional whiplash caused by rapidly cutting between five first dates.
Baker: 1. Joe Millionaire; 2. Dating Around
Kwak: I still ride hard for Blind Date, but this series scratches the same itch, just on a much higher level. If Blind Date was a Motorola StarTAC then Dating Around is an iPhone X.
Bereznak: I associate reality TV shows with the different stages in my life in which I watched them. Right now my favorite show is Bachelor in Paradise, but Dating Around is great because it brings a little bit more dignity and subtlety to the world of dating shows. It’s definitely in my top five now.
McHugh: I don’t feel great about this, but I haven’t really watched reality dating shows since I was a teenager and I loved Next. I guess I have to say this comes in ahead of Next, if only for ethical reasons.
McMullen: The Bachelor is the only other reality dating show I’ve watched and still my no. 1, though I do wish it would incorporate some of the elements of Dating Around—mainly by varying the age of the contestants. It makes such a big difference to watch someone like Gurki, who is 36 and has been married previously, versus someone who is 23 and fresh out of college. It makes for much richer conversation and less orchestrated theatrics.
Sherman: In three hours of television, I grew more attached to each of the six leads (and many of the datees!) than I have ever been attached to the Bachelor at the end of a 20-plus-hour season of The Bachelor. I watched this show with my girlfriend, who I met five years ago on the perfect first date in a bar not too far from where many of these dates were filmed, and I just couldn’t get over how real this felt. It captured so many of the good things and so many of the bad things about meeting random people in random bars across Brooklyn. Nothing will ever displace The Bachelor for me, but that’s only because the prompt says “favorite.” Dating Around may be a better show.
An earlier version of this piece incorrectly stated Jonathan’s song lyrics.
