Dynamic Watchlist Hub: May 09, 2026

10 Best Movies Like The Sure Thing

If you loved The Sure Thing, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

🏆

Expert Review & Ratings

See our full critical analysis and audience score for The Sure Thing.

View Review →
Advertisement
#1
Try Seventeen

Try Seventeen

2002★ 6.2

Why watch this? A perfect follow-up to The Sure Thing for fans of Comedy & Drama & Romance. It captures a similar light-hearted atmosphere.

Teenager Jones has opted not to go to college and is instead renting a room in a boarding house to work on his writing skills. Soon, Jones finds himself dividing his time between t...

#2
Sex Drive

Sex Drive

2008★ 6.4

Why watch this? A perfect follow-up to The Sure Thing for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

A high school senior drives cross-country with his best friends to hook up with a babe he met online....

#3
Grandma

Grandma

2015★ 6.5

Why watch this? A perfect follow-up to The Sure Thing for fans of Comedy & Drama. It captures a similar light-hearted atmosphere.

Self-described misanthrope Elle Reid has her protective bubble burst when her 18-year-old granddaughter, Sage, shows up needing help. The two of them go on a day-long journey that ...

#4
Sacramento

Sacramento

2025★ 6.3

Why watch this? A perfect follow-up to The Sure Thing for fans of Comedy & Drama. It captures a similar light-hearted atmosphere.

When free-spirited Rickey suddenly reappears in father-to-be Glenn’s life, the two former best friends embark on a spontaneous road trip from LA to Sacramento....

#5
Cherry

Cherry

2010★ 6.2

Why watch this? A perfect follow-up to The Sure Thing for fans of Comedy & Drama & Romance. It captures a similar light-hearted atmosphere.

Ivy League Freshman, Aaron Milton (17) gets a different kind of education when he falls for Linda (34) a vivacious former wild-child who has returned to college to straighten out h...

#6
Peggy Sue Got Married

Peggy Sue Got Married

1986★ 6.1

Why watch this? A perfect follow-up to The Sure Thing for fans of Comedy & Drama. It captures a similar light-hearted atmosphere.

At her 25th high school reunion, Peggy Sue faints and awakens in 1960—back in her senior year, before her marriage and all her regrets. Given a second chance to relive her youth, s...

Advertisement