Season 1, Episode 3: "Clubba Hubba"

Mimi is a beautiful, rich girl that Will meets at the country club. Naturally, he needs to endure a My Fair Lady-esque makeover in order to impress her father and win the right to date her, because the patriarchy is the worst.

Season 1, Episode 9: "Someday Your Prince Will Be In Effect, Part 1"

Melinda is fought over by both Carlton and Will in this Halloween two-part episode. Not long after she ultimately chooses Carlton, it's revealed (to Will's great delight) that she's actually a bank thief. Yeah.

Season 1, Episode 9: "Someday Your Prince Will Be In Effect, Part 2"

In the same episode, Will might lose Melinda, but he finds a real life (if very temporary, because this is Fresh Prince) fairytale date in Cindy.

Season 1, Episode 19: "It Had To Be You"

Vivica A. Fox played Jazz's sister and Will's extremely high maintenance and demanding date for the length of one episode.

Season 1, Episode 20: "Nice Lady"

Will escorted the seemingly wholesome daughter of a British lord on a night out — except she turned out to be too wild for Will to handle. Sure, it wasn't quite a date, but we also never heard from her again.

Season 1, Episode 21: "Love At First Fight"

One of Vivian's favorite students quickly descended into an abyss of poor grades after she won Will's affections. Because he just had that kind of effect on people.

Season 3, Episode 6: "P.S. I Love You"

Poor Lindsay thought that throwing lavish gifts at Will would help to buy his affections. And, well, she was kind of right. But thankfully Will also realized that he couldn't accept any of them and begrudgingly returned them to her.

Season 3, Episode 17: "The Best Laid Plans"

This poor young woman told Will that she wanted to wait until she was married before she had sex. So what did he do? He staged a mock wedding officiated by Jazz to make that particular dream come true for the both of them. No wonder she punched him when he came clean before they did the deed.

Season 4, Episode 17: "When You Hit Upon A Star"

Superstar Michelle (played by guest star Stacey Dash) hit on Will after one of her shows because she needed a "reality check." She then ended up giving him a reality check by returning to her former lover.

Season 4, Episode 21: "The Harder They Fall"

Proving that Will had a major thing for women called Lisa, this particular one-time date of his refused to take the next step in their relationship unless he spent time with her extremely terrifying father. You can probably guess how this one ended.

Season 5, Episode 11: "Will Steps Out"

This woman appeared as proof to Will that he actually loved Lisa and most definitely shouldn't be dating other woman. Which, come on, Will. This character totally deserved better than this.

Season 6, Episode 6: "Not, I Barbecue"

Not only did Sandra not appreciate that Will took her to see Showgirls on their date (a movie that Carlton informed her his cousin has seen eight times), but she was also part of that ill-fated double date with Carlton where the two guys had to hide from a man called Mad Dog.

Season 6, Episode 12: "Boxing Helena"

OK, so Helena wasn't a date in any traditional sense of the word. But clearly Will thought he had a chance with the beautiful boxer. You know, right until she whooped his butt — again... and again.

It's a shame that none of these amazing women got to enjoy more than an episode's worth of cheesy pick-up lines and fraught romance with Will to really make them linger in our memories. Or in Will's, for that matter, either.