Tips for lesbians on how to go out with boys

Girls and boys icons

I have always been a lesbian. I have never had a boyfriend. But in my teens and early twenties, I did go out with quite a number of boys (… briefly …). From my own personal experience, I offer some advice on how to proceed.


  • Cross-question your date about his homosexual fantasies and experiences. It’s important to have something in common. You’ll be surprised, with persistence, how much information you’ll discover.
  • Flash the ‘I LOVE MISS WILLIAMS’ tattoo you had etched on your wrist whilst upset at failing your fifth driving test. This will back up your get-out plan when necessary.
  • If you’re planning to enhance your dating experience by fantasising that he is your lesbian crush, choose a clean-shaven, physically refined young man. As a warning, from my diary of Saturday 6th May 1989: “This time I remembered to imagine it was Miss Williams, but with his stubble, height, size, and sweat it didn’t really work.”
  • For an introduction to the local gay scene and an easy get-out, date a gay boy.
  • If you want to have sex with a boy to satisfy your curiosity, do mention this to him beforehand.
  • To avoid that unpleasant goodnight kiss, pummel him with questions about the last woman who broke his heart.


  • If you think you might be a lesbian and you are in love with a beautiful, intelligent, kind girl who is totally into you, don’t sleep with five boys just to make sure.
  • If you have the feeling that the first boy you sleep with should be in some way significant, don’t proposition your university lecturer.
  • In a sexual situation with a boy, don’t play the album of romantic songs sent to you by your female love interest, whilst placing a photograph of your female teacher-crush in your nightgown pocket.
  • Don’t pursue the brother of your female teacher-crush with the intention of getting pregnant by him as a life-long link to his sister.
  • Don’t get off with boys to be contrary, despite your irritation at the sexuality police threatening to throw you out of the university lesbian and gay society.
  • If you have to pretend that boys are girls in order to get turned on, don’t go out with boys.

Going out with boys is a tricky business for a lesbian. Giving advice here is hard and I’m sure I’ve made mistakes. Can you brush up on any of the above? Or do you have any tips of your own to share?

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