Five years ago, a writer friend of mine — we’ll call her Sabrina — got in a fight with her boyfriend after going out with a few friends. She’d partied, she’d danced, she’d accepted free drinks from strangers by giving them the impression she might go home with them. “I’m talking, like, sexy dancing, like, grinding,” she recently recalled. She came home late to her boyfriend of a few years and casually recounted her night. “I was dancing with a couple guys, and obviously nothing happened, but we were grinding and it was really fun,” she remembers telling him. “He was, like, ‘What?’ And I was, like, ‘Yeah, are you not comfortable with that?’”
He wasn’t. You, reader, might not be either. Or maybe you are. Maybe you would have been comfortable with the dancing had it gone down in, say, a salsa class instead of a club? Or if it had been with someone of the same gender? How would you feel if it had happened not with a stranger, but with a mutual acquaintance? What about if the partner in question had a history of infidelity? On Reddit, in group chats, and most definitely in couples therapy, everyone has a different opinion on what exactly is an acceptable level of flirting outside your relationship.
This is largely because, as simple as it might seem, no one can really agree on what flirting is. Personally, I wouldn’t know flirting if it looked me dead in the eye, complimented me, and gave me its number. It’s more of a feeling than an explicitly defined set of behaviors — a combination of physical signals, flowy banter, and tonal subtleties that suggest one person could be sexually interested in another. In the words of my friend Chloe, “It’s hard to describe but easy to feel.” However it’s executed, though, we can generally all agree that flirting signals something specific: I’m interested in you.
But take away that one thing we all associate with flirting — the eventual goal of something romantic — and it becomes awfully murky territory. Some people like it there. For others, it’s a minefield of jealousy, tension, and emotional baggage. How do you define the boundaries of what each partner is comfortable with if there’s no identifiable bullet list of behaviors to work from?
One way to find the line is by crossing it. For months, radio hosts and partners Nico Blitz and Jackie Ramirez had an ongoing argument about Nico’s habit of pouring alcohol down audience members’ throats during DJ sets — which was a little too flirty for Jackie’s liking. “He’s there to create a vibe for a club,” she pointed out, “not one particular person.” In the end, the couple — who later devoted an episode of their podcast, Mexipino, to flirting — couldn’t agree on what it was. “I wouldn’t really consider anything I do flirting unless I’m doing it with an intention,” Nico said, whereas Jackie was more concerned with how his behavior was perceived, intentional or not.
While Nico might define flirting as something he would do only if he were trying to make something happen, other friends suggested nearly the opposite. My friend Katie, who’s been in a monogamous relationship for seven years, told me she thinks of it solely as a fleeting, impersonal interaction, like two sexually unavailable ships passing in the night: “I get to have this random crushlike interaction, and I don’t want either of us to get to know each other past a superficial level.” Once, in a past long-distance relationship, she took things far enough that someone who was definitely not her boyfriend was walking her home, expecting to come upstairs — at which point she realized she’d surpassed the line where flirting ended hours earlier.
This is perhaps what spooks people about flirting while in a relationship: its mere proximity to infidelity. For plenty of coupled people, flirting is a warning sign of — or even a gateway to — more literal adultery. Sometimes that’s true. Chloe — who, like most people I spoke with for this story, didn’t want to use her real name — told me about a flirtatious ex from college who always seemed to have random girls in his house (which he constantly blamed on his roommates), even though she was uncomfortable with how he behaved toward them. He ended up cheating on her, which only validated her suspicions and fueled more jealousy. They stayed together after that, but not for long. “Because I knew he was way more willing to cross those boundaries,” she said, “the flirting made me uncomfortable.” Still, she said, “that’s not necessarily my stance on flirting. It’s more about them being a trustworthy person or not.”
“If you don’t have trust, you don’t have a relationship,” Carly, an office administrator who’s been with her husband for 13 years, seconded. For her, flirty interactions are fair game up until an actual stated invitation to a romantic plan. She and her husband compliment, banter, and dance with other people, she says, within what they both consider reasonable guidelines. What would be too far, I wondered? “An emotional affair. Or, like, sending nudes.” Straight, queer, coupled, single — it seems no one has exactly the same ceiling on what’s okay. Ethan, a tech worker in L.A. who was recently in a throuple with two other men, told me there’s a “sacred first year or two” in a relationship where “if flirting had to happen, I just don’t want to see it. I’m trying to be realistic because I think it will happen regardless.”
Those boundaries don’t just vary from couple to couple — they’re different for each person in the relationship. “My husband is far less territorial than I am,” Daniel, a writer based in L.A., told me, citing a drunken holiday party where he hugged about seven too many straight male co-workers than he needed to, something his husband let slide but that they both knew would have driven Daniel insane had the roles been reversed. Katie’s current boyfriend, she noted, also “knows that I’m more of a jealous person than him.” Although she flirts to her heart’s content while out with her friends (which he’s fine with), she’s glad he’s never shown interest in flirting with other women. “I would never be cool with him acting that way.”
Sabrina, who just got engaged to the aforementioned boyfriend, is still figuring out where each of them draw the line: “There have been instances where I’ve asked for forgiveness rather than permission.” But, she added, “he’s not complaining when I flirt my way into getting our $50 martinis at Bemelmans comped.”
Chloe has also noticed her boyfriend is much more comfortable hearing about her flirtatious encounters when they end in a free drink. “Look, one day we’ll combine our finances and this is for us and our future,” she reasoned. “I tell him, ‘I’m just trying to save so I can buy you a drink sometime.’” While he doesn’t exactly enjoy hearing about instances like this, she said, “he doesn’t say I’m doing anything wrong or crossing a boundary.” That’s one area nearly all couples seem to agree on: Flirting for a higher purpose is, at the very least, tolerated. Sabrina, who’s managed to squeeze a free round of Invisalign out of her dentist just by dialing up the charm, thinks of flirting as a party trick she likes to show off to her now-fiancé — “Hey, look what I can do!”
For others, seeing a partner flirt is a turn-on in and of itself. One colleague mentioned that seeing her husband flirt with people makes her feel like she scored a catch. Carly agreed, if a smidge more cynically: “If you’ve got a shiny toy that somebody else wants … it’s a bit nice!” Daniel said he and his husband have a playfully competitive dynamic when it comes to checking out strangers. “People think when you get married you lose your eyes and your libido,” he said. “That’s not the case.” Still, once you’re deep in a relationship, flirting in the traditional sense does tend to stop — the end goal has been reached, so to speak. But when you watch a partner perform for someone else, they stop being the person who told you their pee smelled weird this morning and suddenly become who they were when you met: a hot stranger who gave you butterflies in your stomach.
Sarah B. Whalen, a New York–based artist, told me watching her husband turn on a little sparkle for someone new is exciting. After six years of dating and three years of marriage, she said, “I know him on all these other levels, and then he puts on this flirty-guy persona, and I’m like, Oh! It’s a version of him I don’t always get, and I like that version.”
One such occasion: During a recent night out at the Crown Heights bar Friends and Lovers, one friend alerted Sarah to a scene that may have distressed some partners: her husband dancing with another woman. “I was, like, ‘Good for him,’” she remembered saying. “He can grind up on whoever he wants. We all know where he’s sleeping tonight.”
More From This Series
- How to Flirt, According to a Bartender
- In Defense of Negging
- 8 People on Their Most Disastrous Flirting Attempts