Hamlet
Hamlet

My (30M) uncle (50sM) may have killed my father (50sM) and now he’s married to my mom (50sF). Should I confront him now or wait until later? [Non-Romantic]

- - -

Penelope
The Odyssey

My husband (45M) went on a road trip twenty years ago and never came back. At what point do I (40F) give up on him and marry one of the men currently trashing my feast room? [Relationships]

- - -

Mr. Rochester
Jane Eyre

I (37M) want to date my governess (18F) but my crazy first wife (30sF) keeps trying to burn the house down. [Relationships]

- - -

Victor Frankenstein
Frankenstein

I (28M) created a freakish abomination that spits in the face of the natural order, now he’s asking me to build him a girlfriend. [Non-Romantic]

- - -

John Proctor
The Crucible

I (30M) slept with my maid (17F) and now she’s accusing my wife (30F) of witchcraft. [Infidelity]

- - -

Elizabeth Bennet
Pride and Prejudice

He (28M) proposed to me (20F), but I just found out he convinced my sister’s (22F) boyfriend (22M) to ghost her. Help! [Relationships]

- - -

Lady Macbeth
Macbeth

I (35F) need help communicating to my husband (39M) that if he doesn’t start pulling his weight in our plot to murder the king, then it’s over between us. [Relationships]

- - -

Lady Anne
Richard III

My (28F) fiancé (32M) just confessed to killing not only my father-in-law but also my husband. Is this a red flag? [Dating]

- - -

Reverend Dimmesdale
The Scarlet Letter

I’m a reverend (35M) and I accidentally got my married girlfriend (27F) pregnant. Should I let her take the blame, or is that kind of a dick move? [Infidelity]

- - -

Cordelia
King Lear

My (25F) dad (80sM) disowned me for refusing to say nice things about him and now my sisters are out of control. [Non-Romantic]

- - -

Olivia
Twelfth Night

I (25F) fell in love with a guy who turned out to be a woman (20sF) in disguise. Luckily for me, she has a twin brother. Should I go for it? [Dating]

- - -

Jay Gatsby
The Great Gatsby

I (32M) left for five years so I could make something of myself and win the heart of the girl I love (23F). Came back to find out she’s married. Should I buy the house across the lake from her and her new husband, or is that weird? [Relationships]

- - -

Lord Henry
The Picture of Dorian Gray

My (35M) friend (??M) is so obsessed with his looks that he sold his soul in exchange for eternal youth, and now he’s just being an asshole about it. How do I address this? [Non-Romantic]

- - -

Othello
Othello

Is my (35M) wife (26F) cheating on me? My friend (28M) thinks she might be. (Turns out she wasn’t, so it looks like I strangled her in our marital bed for nothing.) [Updates]