Photo: FX

This piece originally ran in July 2012. We are re-running it after last night’s date/non-date episode “So Did the Fat Lady.”

“I’m 41 and I’m single. Not really single, just alone,” rang the heavy first note of Louie back in 2010. Tonight’s conclusion of the two-parter “Daddy’s Girlfriend,” which features a riveting turn by Parker Posey as Louie’s newest object of affection, makes it abundantly clear that Louis C.K.’s fictionalized version of himself isn’t as good at submitting to his loneliness as his brazen stand-up tends to imply. The show has presented a series of failed romantic interludes, and the first five episodes of this season all hinge on thwarted attempts to nurture some type of companionship. Vulture examined every single one of Louie’s encounters with love, romance, and being a hapless, solitary fortysomething, and brought you the twenty most interesting ones.

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When: Season one, “Pilot” The Situation: Louie majorly overdresses in a schlubby suit and has no plan as to where they’ll spend the day. “Look, I’m not very good at dating,” he admits. Low Point: Is it when she says “oh God” when he accosts her with a several-minutes-delayed hello kiss, or when Louie starts to weep while making casual conversation about his kids? Nope! It’s the insane moment when Peretti takes off in a helicopter instead of letting Louie make a move on her. Shame Meter: 10. An unendingly awkward date concluding with the most drastic “thanks but no thanks” Louie has ever received and probably will ever receive.

When: Season one, “Poker/Divorce” The Situation: Back in middle school, Tammy beckoned Louie to “whip it out” while sipping Peppermint Schnapps and smoking a cigarette in the woods. He then finds her as an adult through Facebook. Low Point: When Louie finds out his dream of a gorgeous, available adult Tammy is totally off-base, he goes through with it anyway. On her kitchen floor. Shame Meter: 3. Louie makes his choice and sticks with it.

When: Season one, “So Old/Playdate” The Situation: Louie is in from the moment this 26-year-old blonde says, “I’m really turned on by older guys.” Once she unveils her fondness for loose skinned, weird-smelling (“like dying, but sexy”) older males, there’s no going back. “This is the greatest thing that ever happened to me, clearly,” Louie says, right before she tells him she’s not looking for a relationship. Low Point: Louie realizes nothing about him is actually sexy to her; he’s being used for his oldness and his mid-sex anecdotes exemplifying his age. He voted for Dukakis! He remembers $3 movie tickets! He was born in 1967! Shame Meter: 0. No matter how hard he’s been used, even the most shame-prone version of Louis C.K. would find comedy in this. And pride.

When: Season one, “Travel Day/South” The Situation: After having his life saved from the threat of a guy with a gun, Louie’s open to the cop’s subtle suggestion for repayment. “Kiss on the lips’d be nice,” the officer says nonchalantly. “I’m not a homosexual, don’t get the wrong idea. Just like a kiss on the lips is all.” Low Point: Louie obliges. He doesn’t “have a really compelling reason why not.” Shame Meter: 2. One of Louie’s more successful trysts.

When: Season one, “Bully” The Situation: On a bland late-night date at a doughnut spot, Louie avoids a violent encounter with a meathead high schooler by agreeing to say, “You’re very strong and young, I get it, you could kick my ass. I’m sure you could. So I’m really askin’ you nicely to please not kick my ass, okay?” Low Point: “You did the right thing,” Sandra says in one breath, followed up by “If I’m being totally honest, that was a turnoff” in the next. The fatality: “It’s like a primitive thing or something — I mean, you see this guy just totally debase himself, just to be safe? My mind is telling me you are a great guy. But my chemistry is telling me that you’re a loser.” Shame Meter: 8. Possibly more painful than if Louie had just taken the jock’s pummeling.

When: Season one, “Dentist/Tarese” The Situation: Louie fails so hard at making checkout conversation that he loops through the grocery store once more to buy Tarese — a woman he’s blatantly fetishizing and has zero connection with — flowers. Louie stalk-rides home with her on the subway to Harlem, getting called “lil dude” and being asked to “suck a dick, son” along the way. Low Point: Tarese calls out Louie on his creepy, naked attempt to exercise a fetish. “Guess what?” she says. “You don’t get what you want. Not all the time.” Shame Meter: 9. One of Louie’s most misguided attempts at romance.

When: Season one, “Dentist/Tarese” The Situation: A bashful exchange of hellos on Tarese’s stoop, and these two are in bed. Low Point: “I don’t like when I win, sexually, on this show,” C.K. explained in one DVD commentary. Here, Louie learns fantasies are sometimes better unrealized. Shame Meter: 5. It’ll be hard for Louie to boast about this story without feeling the sting of the last one.

When: Season one, “Night Out” The Situation: Mid-date, on a charming walk through Washington Square Park, Lisa reveals she has a child and Louie is ecstatic that they’ve been keeping the exact same secret from each other. Low Point: Lisa is grossed out Louie has kids. “A guy with … a guy with kids? Yeah, I just, wow that’s … that’s a lot. Yeah, that’s … that’s kind of a bummer.” Louie’s left, as usual, stammering. Shame Meter: 7. Louie has to be wondering whether he’ll ever catch a break.

When: Season two, “Bummer/Blueberries” The Situation: Lonesome Louie calls up an associate for a long-shot date, lucks out, then inadvertently participates in the hit-by-a-truck decapitation of a homeless man. Despite his dejected, what-is-life attitude during the flop of a date, Louie walks with Janice on the High Line and accidentally sells her on his awakened existence with blunt lines like “I’m just sick of livin’ this bullshit life.” The camera swirls; they kiss. Low Point: Louie, emboldened and feeling comfortable, reveals that what bent him out of shape was witnessing that gruesome death. And suddenly it’s her story, and she is revolted. “You saw that and then you came out with me? Oh God! I think I need to go home.” Shame Meter: 7. This one’s rough.

When: Season two, “Bummer/Blueberries” The Situation: A fellow parent from Louie’s daughter’s school just wants some uncomplicated, sanitized, “safe and discreet” intercourse. Louie, though baffled, can’t turn it down. He quickly learns Delores is looking for a rent-a-husband — wearing a frumpy nightie, slathering herself methodically with lotion, and kvetching about the PTA, she sends Louie out for condoms (“no spermicide, no lubricant”), some lubricant, Vagitine, and … blueberries. Low Point: In the middle of some no-doubt businesslike foreplay under the sheets, Delores hops to her hands and knees, asks to be spanked (“just hit me, please”) while calling Louie “daddy” in a galactically unsexy fashion, begins to scream “Oh daddy, I’m so sorry” and then bawls. WHAT HAVE WE WALKED INTO? Shame Meter: 10. In a show packed with discomforting moments, this is the absolute cringe-worthiest.

When: Season two, “Joan” The Situation: After losing his casino gig for shit-talking Donald Trump, Louie ends up hanging with the 35-years-his-senior Joan Rivers. They get a little tipsy; she gives him essential career advice about doing the work and surviving. Louie gets turned on enough by her romanticization of comedy and her treating him like both an equal and a student to move in for the smooch. Low Point: It’s actually a success, unless you consider it icky because of Joan’s age. Shame Meter: 1. Whether to his pals or just inside, this is a proud one for Louie, even when he remembers Joan’s initially outraged cry of “I’m older than your grandmother!”

When: Season two, “Come On, God” The Situation: It’s the classic story of the chaste blonde and the “Comedian/Masturbator.” They decide to tolerate each other’s otherness for an evening of drinks, ending with the emotional sharing of Louie’s first sexual experience — simultaneous flatulence/orgasm. They head to her hotel room … Low Point: … when Louie tries his previously successful Joan Rivers Couch Kiss move on Ellen, prompting her to soliloquize on how beautiful their relationship could be with absolute abstinence until marriage. Louie relieves himself in the bathroom. And farts. Shame Meter: 7. This one veers away from misery only in its final instant, when Louie tunes out Ellen’s totally inaccessible concept of a beautiful relationship.

When: Season two, “Duckling” The Situation: On a USO tour of Afghanistan, Louie tries to make conversation with this 19-year-old cheerleader (played by Lily Robbins, whom Louie actually did a USO tour with), striking out when asking if she’s familiar with the work of Led Zeppelin, Van Halen, and Aerosmith. Later he gets a bunch of awwws and smiles out of her by showing off the duckling his daughter smuggled into his luggage. Low Point: She tells him his comedy act is disgusting. “Why can’t you say Christian things and be funny?” Shame Meter: 3. Louie doesn’t get the girl (again), but he gave it his best shot.

When: Season two, “New Jersey/Airport” The Situation: “I wanna show you my pussy,” this automobiled aristocrat tells Louie right off the bat. He hops in her ride and they’re off to New Jersey. Louie’s back in too-good-to-be-true territory. Low Point: Louie either has to have a threesome involving this forward blonde and F. Murray Abraham or bail. In the middle of nowhere. In New Jersey. Shame Meter: 7. Almost too bizarre to process, although Chris Rock and his wife’s tag-team guilting of Louie ups the amperage a bit (“C’mon, man, when’re you gonna grow up? When’re you gonna settle down?”).

When: Season three, “Something Is Wrong” The Situation: They’ve been casually seeing each other for a few months. Low Point: April, flustered to capacity with Louie’s noncommunicative nature, breaks up with herself. “Do you realize that you might be wasting four years of both of our lives because you can’t say bye, see ya right now, because in this second that feels weird?” she begs. Shame Meter: 6. Louie seems happy it’s over, but also like he can’t shake the feeling that he sucks at this.

When: Season three, “Something Is Wrong” and “Miami” (so far) The Situation: They were once married. Now they share custody of their two daughters. Low Point: Presumably their divorce, or the stretch leading up to it. But the phone calls we’ve seen in season three aren’t walks in the park, either. Shame Meter: 8. Janet knows all the shortcuts straight to Louie’s Shame Center.

When: Season three, “Telling Jokes/Set Up” The Situation: Melissa Leo’s tough lady is one of Louie’s oddest romances. Comedian Allan Havey and his wife really missed the mark with this blind-date setup. Low Point: A complicated oral sex standoff resulting in Louie being called gay, having his head smashed into a car window, and being raped. Shame Meter: 10. Despite Louie acquiescing to another date with Laurie (why?), there’s no way he’s not chatting with his therapist about this encounter.

When: Season three, “Miami” The Situation: Ramon rescues Louie while he isn’t drowning, and the two carouse around Miami for the next few days. Low Point: After Louie’s phoned in a favor to his ex-wife so he can stay in Miami longer and get to know Ramon better, Ramon all but asks Louie if he’s gay. The resulting conversation, where nothing is said and everything is awkward, is crushing. Shame Meter: 9. Complicated as usual, only with tons of sexual-orientation anxiety added on.

When: Season three, “Daddy’s Girlfriend Pt. 1” The Situation: Louie’s first onscreen comic-on-comic rendezvous is with the hilarious Maria Bamford. After some unsatisfying sex, Louie asks her to meet his kids. Low Point: “I really don’t wanna do that. I do not wanna meet your kids,” Bamford says, making a complementary vomit-y noise. She polishes it off with a flat, repeated “you’re bad at sex.” Shame Meter: 7. He’s been through worse, but it still stings.