50 More Mature Ways To Leave Your Lover

When Paul Simon suggested “50 Ways To Leave Your Lover” on his 1975 album Still Crazy After All These Years, he clearly wasn’t going through a healthy break up. Then again, how many of us ever do? That would have probably made for a way more boring song.

I’ve been a fan of Simon’s since my friend’s dad played “You Can Call Me Al” in the car on the way home from youth group when I was 12. As I got older and crushes got more complicated, “50 Ways To Leave Your Lover” edged its way into my “I want you, but you have a partner and that sucks so why don’t you ditch them and date me?” musical repertoire. (Alongside “Dontcha” by the Pussycat Dolls and “Pavlov’s Bell” by Aimee Mann.) But as maturity blossomed, I realized dear Paul’s suggestions for how to end a love affair were actually pretty immature. I mean, really? Just hop on the bus, Gus? That’s one way to avoid a painful, yet meaningful and necessary conversation. Sheesh.

So I wondered if I could, in Simon’s style, come up with 50 healthier and nicer ways to terminate a romantic relationship.


1. Have an honest conversation, Nathan.
2. Tell her you want to be just friends, Ben.
3. Don’t make her think she has a chance, Lance.
4. Treat her like an adult, Rolf.
5. Make the break clean, Dean.
6. Don’t date her roommate, Tate.
7. Don’t play games with her heart, Bart.
8. Only to dump her again, Len.
9. Don’t do it while you’re in bed, Ned.
10. Don’t do it at the store, Cor.
11. Don’t do it at the mall, Paul.
12. Show her some respect, Beck.
13. Let her cry, Sy.
14. Don’t be a dick, Rick.
15. Accept her heartbreak, Jake.
16. Don’t send out a tweet, Pete.
17. Don’t Facebook his mom, Dawn.
18. Don’t date his friends, Jen.
19. Don’t fight with his ex, Lex.
20. Give you both time to heal, Neil.
21. Tell her you want to leave, Steve.
22. Pack up your stuff, Russ.
23. Don’t cheat, Marguerite.
24. Understand there will never be “good timing,” Simon.
25. Don’t send a drunk text, Dex.
26. Don’t do it via e-mail, Gail.
27. Sort out your own sh-t, Kit.
28. Don’t place any blame, Jane.
29. Say “It’s not you, it’s me,” Lee.
30. Give her some closure, Rover.
31. Try and stay calm, Ron.
32. Don’t raise your fists, Chris.
33. Don’t insult his body, Dottie.
34. Don’t insult her brain, Blaine.
35. Give him some space, Kase.
36. Don’t make it hurt, Kurt.
37. Give her some reasons, Steven.
38. Don’t make him beg, Peg.
39. Don’t make fun of his cryin’, Ryan.
40. Don’t bring up your affair, Claire.
41. Don’t get her a consolation gift, Cliff.
42. Don’t start accusing him, Jim.
43. Just tell the truth, Ruth.
44. Spare the detail, Dale.
45. Don’t backtrack, Jack.
46. Stay on good terms, Herm.
47. Don’t think about revenge, Ken.
48. Don’t put him through hell, Belle.
49. Share your honest, calm thoughts, Scott.
50. And for the love of sanity, do it face-to-face, Stace. Thought Catalog Logo Mark

More From Thought Catalog