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Conversations about dating, career, confidence, and what it actually feels like to figure life out as you’re living it.

FEATURED

How To Take The Pressure Off Valentine's Day

How long you should text before asking a girl out, plus how to tell when it’s too soon, too late, or exactly the right time.

If You’re New, Start Here

I Don’t Know What I Want To Do With My Career (And That's Normal)

Jan 6, 2026

How To Actually Make Your New Year’s Resolutions Stick

Dec 30, 2025

Why Am I So Nervous To Ask Someone Out In Person?

Dec 23, 2025

For Dating

How To Take The Pressure Off Valentine's Day

Feb 10, 2026

Flirting 101

Feb 3, 2026

Friends vs. Girlfriends, Going Back to Friends, and Modern Dating Rules: Dear Guyset

Jan 20, 2026

Why Am I So Nervous To Ask Someone Out In Person?

Dec 23, 2025

For Confidence & Mindset

Is There Such a Thing as Being Behind in Life?

Jan 27, 2026

How to Become More Interesting

Jan 13, 2026

Is It Bad To Be Jealous of My Friends?

Dec 9, 2025

The Rule of Thirds For Your 20s

Sep 14, 2025

For Work & Career

I Don’t Know What I Want To Do With My Career (And That's Normal)

Jan 6, 2026

How To Feel Confident In Any Room

Dec 2, 2025

What To Do When You Feel Stuck

Nov 24, 2025

How To Introduce Yourself

Nov 11, 2025

Dear Guyset

Friends vs. Girlfriends, Going Back to Friends, and Modern Dating Rules: Dear Guyset

Jan 20, 2026

Getting Ghosted, First Texts, and Rescheduling Dates: Dear Guyset

Nov 18, 2025

First Texts, Falling Fast, and the Little Things: Dear Guyset

Sep 16, 2025

First Dates, Friendships Changing, and Feeling Stuck: Dear Guyset

Jul 22, 2025

Ask Me Anything

This is for the questions you don’t know where to ask.

Ask Me Anything

This is for the questions you don’t know where to ask.