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The Best Dating Movies and TV Shows on Showtime

Finding a good Dating movie and TV show to watch can be hard, so we've ranked the best ones and included where to watch them. Check out our list of the best Dating movies and TV shows of all time streaming on Showtime.

VIEW: best
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1. Meet Joe Black

IMDB LogoIMDB Star
7.2/10
Rotten Tomatoes Logo53%
Reelgood Logo
78/100
Released: 1998Rated: PG-13
Drama, Fantasy

What it's about: When the grim reaper comes to collect the soul of megamogul Bill Parrish, he arrives with a proposition: Host him for a "vacation" among the living in trade for a few more days of existence. Parrish agrees, and using the pseudonym Joe Black, Death begins taking part in Parrish's daily agenda and falls in love with the man's daughter. Yet when Black's holiday is over, so is Parrish's life.

Where to Watch: Available to stream on a popular subscription service (Showtime), stream on a popular TV everywhere service (Showtime) & rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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2. The Crying Game

IMDB LogoIMDB Star
7.2/10
Rotten Tomatoes Logo94%
Reelgood Logo
77/100
Released: 1992Rated: R
Crime, LGBTQ

What it's about: Irish Republican Army member Fergus forms an unexpected bond with Jody, a kidnapped British soldier in his custody, despite the warnings of fellow IRA members Jude and Maguire. Jody makes Fergus promise he'll visit his girlfriend, Dil, in London, and when Fergus flees to the city, he seeks her out. Hounded by his former IRA colleagues, he finds himself increasingly drawn to the enigmatic, and surprising, Dil.

Where to Watch: Available to stream on a popular subscription service (Showtime) & rent or buy from $1.99 on 7 services (iTunes, Google Play & 5 others).

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3. The American President

IMDB LogoIMDB Star
6.8/10
Rotten Tomatoes Logo91%
Reelgood Logo
76/100
Released: 1995Rated: PG-13
Comedy, Drama

What it's about: Widowed U.S. president Andrew Shepherd, one of the world's most powerful men, can have anything he wants -- and what he covets most is Sydney Ellen Wade, a Washington lobbyist. But Shepherd's attempts at courting her spark wild rumors and decimate his approval ratings.

Where to Watch: Available to stream on a popular subscription service (Showtime), stream on a popular TV everywhere service (Showtime) & rent or buy from $3.99 on 7 services (iTunes, Google Play & 5 others).

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showtime

4. My Best Friend's Wedding

IMDB LogoIMDB Star
6.3/10
Rotten Tomatoes Logo73%
Reelgood Logo
75/100
Released: 1997Rated: PG-13
Comedy, Romance

What it's about: When she receives word that her longtime platonic pal Michael O'Neal is getting married to debutante Kimberly Wallace, food critic Julianne Potter realizes her true feelings for Michael -- and sets out to sabotage the wedding.

Where to Watch: Available to watch free online (IMDb TV), stream on a popular subscription service (Showtime), stream on a popular TV everywhere service (Showtime) & rent or buy from $2.99 on 8 services (iTunes, Google Play & 6 others).

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hulu_plus

5. Step Up

IMDB LogoIMDB Star
6.5/10
Rotten Tomatoes Logo20%
Reelgood Logo
71/100
Released: 2006Rated: PG-13
Drama, Musical

What it's about: Everyone deserves a chance to follow their dreams, but some people only get one shot. Tyler Gage is a rebel from the wrong side of Baltimore's tracks and the only thing that stands between him and an unfulfilled life are his dreams of one day making it out of there. Nora is a privileged ballet dancer attending Baltimore's ultra-elite Maryland School of the Arts

Where to Watch: Available to stream on a popular subscription service (Showtime & Hulu), stream on a popular TV everywhere service (Showtime) & rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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epix

6. Charlie Bartlett

IMDB LogoIMDB Star
7.0/10
Rotten Tomatoes Logo57%
Reelgood Logo
71/100
Released: 2007Rated: R
Comedy, Drama

What it's about: Awkward teenager Charlie Bartlett has trouble fitting in at a new high school. Charlie needs some friends fast, and decides that the best way to find them is to appoint himself the resident psychiatrist. He becomes one of the most popular guys in school by doling out advice and, occasionally, medication, to the student body.

Where to Watch: Available to stream on a popular subscription service (Showtime), stream on a popular TV everywhere service (Showtime & Epix) & rent or buy from $2.99 on 7 services (iTunes, Google Play & 5 others).

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amazon_prime
showtime
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7. Elizabethtown

IMDB LogoIMDB Star
6.4/10
Rotten Tomatoes Logo29%
Reelgood Logo
66/100
Released: 2005Rated: PG-13
Comedy, Drama

What it's about: Drew Baylor is fired after causing his shoe company to lose hundreds of millions of dollars. To make matters worse, he's also dumped by his girlfriend. On the verge of ending it all, Drew gets a new lease on life when he returns to his family's small Kentucky hometown after his father dies. Along the way, he meets a flight attendant with whom he falls in love.

Where to Watch: Available to watch free online (Tubi TV), stream on a popular subscription service (Prime Video, Showtime, CBS All Access & 1 other), stream on a popular TV everywhere service (Showtime & Epix) & rent or buy from $2.99 on 8 services (iTunes, Google Play & 6 others).

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8. Midnight Sun

IMDB LogoIMDB Star
6.6/10
Rotten Tomatoes Logo22%
Reelgood Logo
62/100
Released: 2018Rated: PG-13
Drama, Romance

What it's about: Katie, a 17-year-old, has been sheltered since childhood and confined to her house during the day by a rare disease that makes even the smallest amount of sunlight deadly. Fate intervenes when she meets Charlie and they embark on a summer romance.

Where to Watch: Available to stream on a popular subscription service (Showtime), stream on a popular TV everywhere service (Showtime) & rent or buy from $2.99 on 8 services (iTunes, Google Play & 6 others).