Make Awkward Talks Less Painful with this 8-Step Awesome Cheat Sheet 📜
Dating requires many awkward conversations–whether it’s...
...asking for the next date
...talking about STIs
...discussing how much to be in contact
...when to have sex
...how to introduce your kids into the mix
...when to be monogamous…
IT’S ALWAYS SOMETHING!
And we, as humans, are awkward about these kinds of topics.
From 20 years of coaching daters in The Handel Method® I can tell you what works best when there’s an awkward conversation to be had, and this cheat sheet will help you when you have to have one in real life…
You have to get your point across clearly while being graceful enough that the other person wants to listen. And you have to plan it out and make sure to follow all the steps, that’s why I made this cheat sheet for you!
Read each step below and apply it to your situation. I gave some examples so you’d get the idea of how it sounds.
First you ask permission, or else it’s an ambush.
Then you state a positive intention to put the person at ease.
To put you at ease, you can state any fears you have.
If there is anything for you to own, do it up front because it paves the way even more.
Enough preamble…spill the beans next!
Don’t forget the part where you try to get the other person talking and listen carefully to their response. This is where the gold (communion!) happens! You can even say back what you heard to make sure.
Lastly, be specific about agreements going forward so it doesn’t feel like there are any loose ends.
The following chart is visually condensed to be readable on mobile, but here is a downloadable PDF that you can save and/or print out, to use for filling in your own answers.
Difficult conversations are, well…difficult 😂 but with practice you can learn to do them like a pro. It will make you MUCH less scared of relationships-- which will make you a much better dater.
You’ve got this!
If you want to learn more about how to communicate, take my online course: Master the Art of Love and take advantage of the group discussion forum as you go through the real life drama of dating and difficult conversations.
Want to Make Awkward Dating Talks Way Less Painful?
Hard conversations don’t have to be dealbreakers. My free training will show you how to handle tough topics—like sex, commitment, or boundaries—with clarity, confidence, and grace.
✅ Learn the 8-step cheat sheet for any awkward convo
✅ Communicate your truth without scaring someone off
✅ Turn hard talks into closer connection, not confusion
Frequently Asked Questions about Awkward Conversations in Dating
1. Why do awkward conversations matter so much in dating?
Because how you communicate early on sets the tone for the entire relationship. If you avoid hard topics, you risk misalignment, resentment, or heartbreak down the line.
2. What if I’m afraid I’ll scare someone off?
Then it’s even more important to use the 8-step structure. When you lead with care, honesty, and curiosity, the right person won’t run—they’ll lean in. And if someone bolts, they probably weren’t emotionally ready.
3. Should I bring up serious stuff like STIs or exclusivity early?
Yes—when the timing is right. Awkward doesn't mean inappropriate. Being upfront (with kindness) protects both of you and builds trust. It’s not about dumping info—it’s about shared safety and understanding.
4. What’s the hardest part of these convos—and how do I get better at it?
Usually it’s the fear of being judged or rejected. The solution? Practice. Use the cheat sheet, rehearse what you want to say, and ask permission before diving in. Each time you do it, it gets easier.
5. What if the other person shuts down or gets defensive?
Stay calm. Reflect back what you’re hearing and remind them of your intention. If someone can’t have a respectful conversation, that’s useful data for you. You deserve a partner who can talk with you, not around you.
