The Oscar-nominated actor's first credited role was as (literally) smoking-hot Jake, who picks Carrie up in Season 2. Things go great during the ride in his Porsche, but then she puts the brakes on their night out after he sees her unfortunate photo on the cover of New York magazine.

Prior to marshalling up justice on FX's Justified, Timothy Olyphant nabbed Carrie's attention as twentysomething Sam. He may have seemed great under the neon haze, but in the bright light of day, he showed his immature age.

Appearing in the first Sex and the City episode following the 9/11 attacks, the Graceland star played charming sailor Louis, who invited Carrie and her friends to a Fleet Week soireé. After he reveals tepid feelings toward the Big Apple, Carrie decides to spend the night with her great love, New York City, instead.

As the polar opposite of the slick-haired attorney Harvey Specter in Suits, Gabriel Macht played Barkley, an artist with a taste for models (and Samantha) in the first season of the HBO comedy.

Best known for his integral part in the Marvel Cinematic Universe as Agent Phil Coulson, Gregg appeared on Sex and the City at a speed-dating session with Miranda. He acted as an ER doctor while Miranda pretended to be a stewardess. Though neither of them were being truthful about their backgrounds, they still had a few fun nights together.

Before taking the role of Mad Men lothario Roger Sterling, Slattery portrayed silver fox politician Bill Kelley, who Carrie dated until he couldn't handle how prospective voters would perceive her column.

The Leftovers star actually appeared on Sex and the City twice as two completely different suitors for Carrie. While he flirted with her in Season 1 as Stanford's friend Jared, his bigger role was in Season 2 as Vaughan who, unfortunately, had problems in the bedroom.

True Detective wasn't Vince Vaughn's first foray into an HBO show. He guest-starred as supposed Hollywood agent Keith Travers, who, in reality, was Carrie Fisher's personal assistant. The other Carrie abruptly discovered this when Fisher found them together in her house.

In his first TV role, Will Arnett of Arrested Development fame worked his magic on Miranda as they bonded over historical biographies. Things fizzled out quickly, however, when his habit of hooking up in public got too weird.

Currently sleazing it up as the crooked mayor of Vinci on True Detective, Ritchie Coster played Trey's dashing Scottish groomsman who catches Samantha's eye. Too bad she could never quite catch what he was saying because of his thick accent.

Way before embodying Mayhem in those Allstate commercials, Dean Winters portrayed John, Carrie's go-to friend with benefits. Not so shockingly, Carrie soon realizes that their connection in the bedroom doesn't match up to their connection in every other department.

Dominic Fumusa of Nurse Jackie and the upcoming Michael Bay movie 13th Hour guested as Carrie's ex and Miranda's beau. Miranda, unfortunately, didn't heed Carrie's warning until she realized for herself how much of a jerk he really was.

Bobby Cannavale may have won an Emmy for his role on HBO's Boardwalk Empire, but he first appeared on the premium cable network as Adam Ball, Samantha's flavor of the week whose actual flavor she didn't care for very much.

Known best as Dr. Hank Lawson on Royal Pains, he appeared in one episode of the HBO comedy as Miranda's squeeze Josh, who just couldn't get it going for her. And so, though he tried his best, he didn't last long.