An awkward Connecticut professor tries to cure his loneliness by dating tens of women, all to no avail.

Sitting at a bar, a man reminisces about his past experiences with love and develops a philosophy for 'beautiful' relationships that relies on the inevitability of their ends.

A middle-aged writer turns back the clock by twenty years and narrates his ill-fated romance with the beautiful but unattainable girl from his memories.

A college sophomore meets a thirty-something-year-old guy while working. Despite being exciting initially, the relationship heads towards uncomfortable territory.

A couple who met online eventually move in together in New York City, but overtime, their relationship completely falls apart.

As a strictly sexual affair stretches past its expiration date, a woman and her taken lover struggle to define their burgeoning feelings for each other.

While working through the complexities of her past relationship with her ex-husband, a woman considers her current boyfriend's marriage proposal as she prepares for a graveyard picnic.

An extremely attractive man is fascinated by a woman he describes as 'unattractive.' He is certain that he will be the one to end their relationship - but as time passes, he learns that breaking a heart is also a kind of heartbreak.

Coworkers at a newspaper gleefully tease one of their peers for his constant stream of passionate affairs, culminating in an intervention when he brings back from Spain the most ludicrous girlfriend yet.

A young college student is visited by his girlfriend for his birthday when they learn that they’ve unfortunately outgrown each other since he’s been away.