Dynamic Watchlist Hub: Apr 14, 2026

10 Best Movies Like Sincerely, Harold Washington

If you loved Sincerely, Harold Washington, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

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Expert Review & Ratings

See our full critical analysis and audience score for Sincerely, Harold Washington.

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#1
The Perfect Date

The Perfect Date

2019★ 6.4

Why watch this? A perfect follow-up to Sincerely, Harold Washington for fans of Romance. It captures a similar light-hearted atmosphere.

No beau? No problem! To earn money for college, a high schooler creates a dating app that lets him act as a stand-in boyfriend....

#2
After Ever Happy

After Ever Happy

2022★ 6.8

Why watch this? A perfect follow-up to Sincerely, Harold Washington for fans of Romance. It captures a similar emotionally gripping atmosphere.

As a shocking truth about a couple's families emerges, the two lovers discover they are not so different from each other. Tessa is no longer the sweet, simple, good girl she was wh...

#3
My Fake Boyfriend

My Fake Boyfriend

2022★ 5.9

Why watch this? A perfect follow-up to Sincerely, Harold Washington for fans of Comedy. It captures a similar light-hearted atmosphere.

A young man in a tricky situation follows the advice of his unconventional best friend and uses social media to create a fake boyfriend to keep his awful ex-lover out of his life. ...

#4
Casanova

Casanova

2005★ 6.4

Why watch this? A perfect follow-up to Sincerely, Harold Washington for fans of Adventure. It captures a similar light-hearted atmosphere.

With a reputation for seducing members of the opposite sex, regardless of their marital status, a notorious womanizer discovers a beauty who seems impervious to his charms. However...

#5
Marked Men: Rule + Shaw

Marked Men: Rule + Shaw

2025★ 6.6

Why watch this? A perfect follow-up to Sincerely, Harold Washington for fans of Romance. It captures a similar emotionally gripping atmosphere.

Shaw Landon has loved Rule Archer from the moment she laid eyes on him. Rule, a fiery-tempered rebel tattoo artist, doesn’t have time for a good girl pre-med student like Shaw — ev...

#6
Endless Love

Endless Love

2014★ 6.9

Why watch this? A perfect follow-up to Sincerely, Harold Washington for fans of Drama. It captures a similar emotionally gripping atmosphere.

A privileged girl and a charismatic boy's instant desire sparks a love affair made only more reckless by parents trying to keep them apart....

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