Topics

Dating and first times

Chemistry, situationships, casual sex, and first-night nerves.

How to Ask Someone Back to Yours Without a Court Summons Energy

How to ask someone back to yours. Jessica's lines from the pavement and the last-orders crush.

6 September 2026Jessica Simpkin

Dating and first times

First Time Sex Nerves, Even When It Is Not Your First Time

First time sex nerves: what Jessica does with the shake, the overthinking, and the silence.

27 March 2026Jessica Simpkin

Dating and first times

How to Make the First Move When You Were Taught to Wait

How to make the first move: a hand, a line, a kiss. Jessica on the times she waited and the time she did not.

23 March 2026Jessica Simpkin

Dating and first times

First Time Sex With a New Partner, Even If You Are Not New to Sex

First time sex with a new partner: nerves, bodies, and Jessica’s first-night checklist.

19 March 2026Jessica Simpkin

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

What Is a Situationship? I Have Been in Three and Only Named One

What a situationship is, how to spot one, and Jessica on the almost-relationship she let drift.

11 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

How to Flirt in Person When You Are English and Therefore Reserved

How to flirt without a script from a film. Jessica on eyes, timing, and the joke that works.

4 March 2026Jessica Simpkin

Dating and first times

How to Have Sex for the First Time Without Treating It Like an Exam

How to have sex for the first time: nerves, logistics, and Jessica’s own clumsy first.

28 February 2026Jessica Simpkin

Dating and first times

When to Kiss on a First Date, and When I Should Have Waited

When to kiss on a first date. Jessica on doorsteps, last trains, and reading the room.

18 December 2025Jessica Simpkin

Dating and first times

11 Signs They Want to Sleep With You, and 4 That Are Just Being Nice

Signs they want to sleep with you, minus the TikTok nonsense. Jessica on reading adults.

14 December 2025Jessica 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

14 Red Flags in Dating I Used to Call Chemistry

Red flags in dating, including the ones Jessica excused because the sex was good.

28 November 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

Dating and first times

How to Write a Dating Profile That Gets Dates, Not Just Likes

How to write a dating profile that gets dates, not just likes. Look like yourself after work, and write one true thing they can answer.

16 November 2025Jessica Simpkin

Dating and first times

How to Turn a Hookup Into a Relationship Without a Campaign

How to turn a hookup into a relationship: timing, honesty, and Jessica’s almost.

12 November 2025Jessica Simpkin

Dating and first times

How to Text After a Hookup Without Writing a Constitution

How to text after a hookup. Jessica's timing, length, and the message she wishes she had sent.

5 November 2025Jessica Simpkin

Dating and first times

How to Start Dating After a Long Relationship Without Comparing Everyone to Them

How to start dating after a long relationship. Jessica on the first app reopen and the first kiss that felt new.

1 November 2025Jessica Simpkin

Dating and first times

How to Kiss for the First Time When Your Brain Has Left the Building

How to kiss for the first time: lean in, miss, laugh. Jessica on first kisses that were not cinematic.

20 October 2025Jessica Simpkin

Dating and first times

How to Date Casually Without Catching Feelings on a Schedule

How to date casually on purpose. Jessica on calendars, other people, and telling the truth.

18 September 2025Jessica Simpkin

Dating and first times

How to Ask Someone Out Without a Three-Week Internal Meeting

How to ask someone out: one clear question. Jessica on the times she delayed and the time she did not.

14 September 2025Jessica Simpkin