After multiple unsuccessful attempts at asking out our anonymous lady, the guy on date No. 22 finally won her over with the promise of sushi and tales of adventure. But did he deliver?

A wedding coordinator walks into a bar … and forgets whom she’s meeting for Date No. 24.

We kick off our new Hawai‘i dating series with Date No. 1, which—spoiler alert!—didn’t end well.

Or how we realized that great connection was merely platonic. Welcome to date No. 2—one that by all accounts should have ended well.

Date No. 14 had quite a few red flags, but this dater was determined to give it a shot for love.

Date No. 3 in our series was heading in the right direction until a surprise visitor killed the vibe.

Date No. 21 is our first submission about attempting to date during quarantine—something we don’t recommend (seriously. Stay home).

The boy from Date No. 9 was everywhere—until it came time to pick up the check.

Date No. 20 took our former college party gal on a whirlwind date that lasted well past sunrise.

Just because the girl was on a date with another guy doesn’t mean Dater No. 16 wasn’t gonna shoot his shot.

Dater No. 13 set herself a dating challenge and met her perfect match. But not before matching with a real challenge.

Unlike date No. 9, the gentleman on date No. 10 knows how to pick up the check—even when it’s for more than he bargained for.