Getting Back Into Dating After a Break

Whether you're trying to work up the nerve to ask out your office crush, figuring out what you actually want in bed, or navigating a decades-long relationship that's hit a sexual wall — the answer almost always comes back to the same thing: you have to be willing to go there. Say the thing. Ask the question. Have the conversation you've been putting off.

In this episode, I'm taking listener calls on everything from the first nervous steps back into dating to the hard conversations that long-term couples are too scared to start.

In this episode, you'll learn:

• Why dating is a muscle — and what to actually do when you've been out of the game so long that even asking someone out feels impossible

• What really happens to a vulva when a woman is fully aroused, why morning sex resentment is almost never just about morning sex, and what to do when your sexual awakening happens 20 years into a committed relationship

• How to talk to your kids about sex early and often in a way that builds confidence instead of shame — starting with something as simple as using the right words for their body parts

More Dr. Emily: 

• Shop With Emily! Explore Emily’s favorite toys, pleasure accessories, bedroom essentials, and more — designed to support your pleasure and confidence. Free shipping on orders $99+ (some exclusions apply).5

• Interested in 1:1 Coaching with Emily? Go to sexwithemily.com/coaching to apply! 

• Sex With Emily Guides: Explore pleasure, deepen connections, and enhance intimacy using these Sex With Emily downloadable guides.

• The only sex book you’ll ever need: Smart Sex: How to Boost Your Sex IQ and Own Your Pleasure

• Want more? Visit the Sex With Emily Website

• Let’s get social: Instagram | X | Facebook | TikTok | Threads | YouTube

• Let’s text: Sign up here

• Want me to slide into your email inbox? Sign Up Here for sex tips on the regular.

Chapters:

0:00 - Intro

2:07 - How to Ask Out an Office Crush Without Overthinking It 

6:06 - Breaking Out of the Friend Zone on a First Date 

9:43 - She Engorged During Orgasm — What Just Happened? 

15:21 - Embracing What Sex Actually Looks and Feels Like 

16:07 - Boyfriend Wants Her to Sleep with Someone Else — Does She Have To?

18:42 - Resentful About 5:30 a.m. Sex & Never Having Orgasms 

22:23 - Sexual Awakening, Open Relationship Fallout & Staying or Going

26:35 - How to Raise a Sex-Positive Son Without Shame 

Learn more about your ad choices. Visit megaphone.fm/adchoices