This week, we’re talking about worst first dates, dating red flags, and the kind of situations that make you rethink how people move when it comes to relationships.

From being put in uncomfortable positions on a first date to realizing someone isn’t as single as they claimed, this conversation gets into boundaries, awareness, and recognizing when something just isn’t right. We also talk through the pressure people feel in dating and how quickly things can go left when basic respect and communication are missing.

If you’ve ever questioned your dating experiences, struggled with boundaries, or felt like people are moving a little too wild in today’s dating world, this episode will help you feel less alone and more aware of what to look out for.

We also touch on everyday situations outside of dating, like dealing with people at work, navigating petty conflicts, and understanding how small decisions can turn into bigger problems when communication and respect aren’t there.

New episodes every Wednesday. Follow the podcast everywhere you listen.

Timestamp

[00:00:00] Looking back at early episodes + podcast growing pains

[00:03:10] Question of the Week: Worst first dates

[00:04:05] Date turns into unexpected childcare situation

[00:07:05] Apartment full of candles + immediate red flags

[00:08:45] Bathroom situation that makes everything worse

[00:09:50] Standing outside… something feels off

[00:10:30] Would you have gone inside? Breaking down the decision

[00:14:10] Finding out your date isn’t actually single

[00:16:30] When relationship drama pulls you into situations you didn’t ask for

[00:20:35] First date turns into a permanent mistake

[00:22:00] That moment crosses a serious line

[00:25:05] Showing up to a date… and the whole family is there

[00:26:40] When the situation just keeps getting worse

[00:27:30] Breaking down how strange that entire date was

[00:31:20] Getting banned online for no reason

[00:33:00] What even counts as “breaking the rules”?

[00:35:05] Coworker tension over something small

[00:36:30] Splitting costs, expectations, and petty reactions

[00:37:45] Why situations like this turn into bigger issues

[00:40:05] When small disagreements become unnecessary conflict

[00:43:10] Final thoughts + wrapping up

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#69 - The Worst First Dates We’ve Ever Heard