Jessica Simpkin

The archive

Writing

First-person answers to the questions people actually type into Google. One story, then the useful bit.

Showing posts tagged casual sex · All writing

Dating and first times

Friends With Benefits Rules I Learned by Breaking Them

Friends with benefits rules that keep it kind. Jessica on the friendship she nearly lost.

15 March 2026Jessica Simpkin

Dating and first times

How to Have Casual Sex Without Pretending You Have No Feelings

How to have casual sex with rules you can live with. Jessica on the arrangements that stayed kind.

7 March 2026Jessica Simpkin

Dating and first times

Sex on the First Date: When I Have, When I Have Not, What Changed

Sex on the first date. Logistics, judgement, and Jessica's actual nights, not a moral.

2 December 2025Jessica Simpkin

Dating and first times

One Night Stand Etiquette for People Who Were Raised With Manners

One night stand etiquette: leaving, staying, water, and Jessica's worst goodbye.

24 November 2025Jessica Simpkin