PHOTOS: 40 Things Every Gay Man Should Do Before Turning 40

Getting older is never easy. For many gay men the idea of turning 40 is nothing short of terrifying. We ask ourselves the big questions, “What have I done with my life? What have I accomplished? Why is no one responding to my OKCupid profile?” Our life experience checklist will continue to grow as we get older. Here are 40 things every gay man should do before turning 40.



1. Go to a gay pride parade.


2. Get over your body issues and be a go-go dancer for a night.


3. Dress up in drag.


4. Dress up in leather.


5. Accept that you will never have sex with Jake Gyllenhaal.


6. Go to a gay wedding.


7. March in solidarity with your gay brothers and sisters at a protest rally.


8. Go to an LGBT Film Festival.


9. Donate to The Human Rights Campaign, The Trevor Project, Gay Men’s Health Crisis or other gay advocacy organization.


10. Go to your class reunion and finally talk to the straight guy you were obsessed with in high school.

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11. Expand your horizons. Find a fetish.


12. Read And the Band Played On, Tales of the City, Running with Scissors, Middlesex, and A Single Man.


13. Stop wearing t-shirts that are two sizes too small.


14. Date someone that is at least 10 years older than you.


15. Date someone that is at least 5 years younger than you.


16. Know your queens! RuPaul, Vaginal Davis, Divine, Lady Bunny, Dame Edna, Jackie Beat, Sylvester, Alexis Arquette, Candy Darling, Miss CoCo Peru, Leigh Bowery and The Lady Chablis.


17. Stop being afraid of lesbians.


18. Live with a boyfriend.


19. Go to a Broadway musical.


20. Go to an NFL, NBA or pro baseball game. (Yes, really!)


21. Go to therapy.


22. Have sex on a beach, in a park, in an elevator, on a roof, in a car, in the desert, and your parent’s house.


23. See these films: Weekend, The Broken Hearts Club, Trick, ShortBus, Get Real, Longtime Companion, The Celluloid Closet, Milk, BridegroomThe Rocky Horror Picture Show, The Boys in the Band and The Wizard of Oz.


24. Volunteer at an LBGT Senior Center.


25. Be in a monogamous relationship.


26. Be in an open relationship


27. Take a same-sex Latin, Swing or Ballroom dance class.


28. Stay friends with a former lover.


29. Break out the cheesecake and watch every episode of The Golden Girls. (Add a pint of ice cream if you can make it through the spin-off, The Golden Palace.)


30. Have sex in a foreign country.



31. Have sex with someone who doesn’t speak English. (All the better if you can combine this with number 30.)


32. Sing a Steve Nicks song at karaoke. (And it can’t be Landslide!)


33. Make peace with your parents.


34. Know your status. Get an HIV test.


35. Go to an adult bookstore or movie theater. (We recommend wearing close-toed shoes.)


36. Fall in love.


37. Have sex with a woman just so you can say you did.


38. Take your boyfriend home for the family Thanksgiving.


39. Stop manscaping everything!




  • Sean Brown

    Why is turning 40 terrifying? I felt great when I turned 40! The best thing about being 40 is watching the younglings try to keep up with me! Lol!

  • Luis Henrique

    im turning 49 !! on 27-october Sean Brown and it gets BETTER lol.. the more secure I become; the more attraction i get … loving it .. and yeah,, the hottest boyz lov daddy; silver fox; etc etc I HAVE ARRIVED my friend..

  • juan

    That’s very beautiful. I have a best friend like that. She’s like my sister. We have never had sex but are super close. Those ones are unforgettable. 🙂

  • naturfun

    I am over 40 now and I have done every one of those things (except a couple of the suggested books and movies). I have always lived life to the fullest. One thing I didn’t see on the list that should be here is to have group sex at least once.

  • naturfun

    I came out at 26 and I dated a 40yo guy, then when I was 33 I dated a 20yo, and I guess that’s somehow a lot of guys’ sequence. As an older gay guy, I think some of you criticizers are a little too harsh. It’s different now in this generation, with gay marriage, gays adopting kids, and more equality. When I was growing up, these things were a part of our journey to find ourselves and not stereotypes then, and with the free love attitude in the 70s and 80s you could have sex in a lot of different places and ways (and yes, there was probably a lot less enforcement of public sex rules etc., than today, due to today’s health reasons and more mainstreaming of the gay lifestyle. Maybe another list thing might be to try a drug (not meth, but I tried marijuana, cocaine, speed and ecstasy when I was on the way to becoming the much more conservative gay man I am today.

  • wane

    My bf thought we were #36.

  • Anonymous

    always had love affairs m/f and my best one was during 3 wild years in my 50′, he was 12 years younger ….. cash your dreams before they slip away ,i realize now how many things i missed . and now game is over ..