Is It Normal to Regret Only Dating One Person?

This week’s Questions of the Week episode gets DEEP.

You all sent in some of the most emotional, complex, and honest questions we’ve ever answered, especially around:

• What to do when you don’t like your partner’s friends
• Whether we ever regret only dating each other
• How to know when it’s time to leave a relationship
• How our finances changed after becoming entrepreneurs
• Navigating alcohol, health changes, and lifestyle shifts
• The “are we official?” conversation
• Our age gap and how it’s affected our relationship
• The funniest moments, biggest purchases, and dream NYC business

This episode is personal, vulnerable, and full of advice we wish we had years ago.

So settle in, get cozy, and grab your chai. 💛

New episodes every Monday at 7 am. Don’t forget to subscribe, and as always, we love you! Thank you for spending your Monday with us 💛

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Time codes

0:00 - WELCOME TO HALF PAST CHAI

3:33 - Have you NOT liked your partners friends?

8:27 - Do you regret only dating each other?

12:43 - How do you know it’s time to break up?

14:17 - What do finances look like now that you're self-employed?

17:23 - How much do we make on YouTube & Instagram?

18:47 - Why did we stop drinking alcohol?

22:15 - Funniest experience we’ve had together

25:18 - Does Suketu like running as much as Hallie?

25:39 - Do you apply your Data Science skills now?

26:22 - How do you ask someone to be your BF/GF?

28:24 - What is one quality each of you love about each other?

29:31 - Does your age gap affect your relationship?

31:04 - Most the ridiculous purchase you made as a couple

31:44 - If you guys could open up a shop in New York City, what would it be?