Dating Archives

dating

50+ Gay Questions To Ask on a First Date

A collection of 50+ gay first date question prompts to get the conversation flowing.

Kayla Kumari Upadhyaya

Jan 2, 2026

two Black women are smiling while asking each other questions on a first date

dating

50+ Gay Questions To Ask on a First Date

A collection of 50+ gay first date question prompts to get the conversation flowing.

Kayla Kumari Upadhyaya

—

Jan 2, 2026

dating

Against Dating Around the Holidays

Holiday dating has a glow to it, the way everything looks better under low light. It’s easy to mistake that glow for connection.

Titeänyä Rodríguez

—

Dec 22, 2025

dating

‘I’ve Dated Men for Three Decades. Is it Too Late To Start Dating Women?’

“I am a 50 year old woman who has exclusively dated men for the last 30 years. I dated a girl in highschool but it was a different (and very…

Kayla Kumari Upadhyaya

—

Nov 25, 2025

dating

A Queer Guide to Cuffing Season

I used to chase warmth in ways that weren’t always safe for me — staying too long, giving too much, confusing chaos for chemistry. These days, warmth means choosing softness…

Titeänyä Rodríguez

—

Nov 17, 2025

af+

My Girlfriend’s Ex Sent Me a Warning Message. Should I Hear Her Out?

Your new girlfriend’s ex has tracked you down and has some things to tell you! Also, how to stay COVID-safe while getting more involved in queer kink communities.

the team

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Oct 24, 2025

af+

Was I A Fool To Think They’d Kiss Me Back?

You made the first move and have felt weird about it ever since. Also — needing tips on dating in your mid-30s, ’cause it’s not going well so far.

the team

—

Oct 17, 2025

dating

‘Am I Being Breadcrumbed Into a Situationship?’

With the boom of online dating, many young adults are finding themselves in situationships.

Summer Tao

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Oct 14, 2025

af+

Help I Have a Crush On My Ex-Boyfriend’s Sister

Should you make a move on an ex-boyfriend’s sister who may or may not be your root? Also — tips on sexting A WRITER.

the team

—

Sep 19, 2025

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Dating

dating

50+ Gay Questions To Ask on a First Date

50+ Gay Questions To Ask on a First Date

Against Dating Around the Holidays

‘I’ve Dated Men for Three Decades. Is it Too Late To Start Dating Women?’

A Queer Guide to Cuffing Season

My Girlfriend’s Ex Sent Me a Warning Message. Should I Hear Her Out?

Was I A Fool To Think They’d Kiss Me Back?

‘Am I Being Breadcrumbed Into a Situationship?’

Help I Have a Crush On My Ex-Boyfriend’s Sister

Become a Member

What You Get:

Become a Member

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Dating

dating

50+ Gay Questions To Ask on a First Date

Become a Member

What You Get:

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