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Dating Intentionally

267. The Unexpected Truth About Finding Love Later In Life w/ Sandy Weiner

Dating Intentionally

Talia Koren

Education, Relationships, Society & Culture, Self-improvement

4.7596 Ratings

🗓️ 29 May 2026

⏱️ 58 minutes

🧾️ Download transcript

Summary

I'm chatting with Sandy Weiner, a dating coach who has spent 13 years helping people date after divorce, and started her own dating journey at 52 after leaving a 23-year marriage. We're discussing everything from knowing when you're actually ready to date again to navigating the "jaded factor" in midlife dating to having the dating conversation with your kids (at any age). Sandy also shares why being picky about what matters and wide open about what doesn't is the mindset shift most people miss, plus how she creatively meets people offline through meetups, classes, and even emailing her network with her dating profile. At the end, we tackle a dating dilemma from a 51-year-old single mom in a casual situation with a separated 43-year-old, and whether she should walk away or stay.


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Transcript

Click on a timestamp to play from that location

0:00.0

Welcome back to dating intentionally. I'm Talia, and I'm here with no nonsense

0:08.8

advice for navigating dating and relationships with confidence and ease, whether you've

0:13.3

been dating for a while or you're just starting out. I believe dating can be fun,

0:17.1

and I'm here to help you enjoy the process. Today I'm talking with Sandy Weiner,

0:21.4

the host of Last First Date Radio, a podcast that's been running for 13 years, which is

0:26.6

remarkable. Sandy is a dating coach who specializes in helping people a date with intention

0:31.2

after divorce and a midlife. She started her coaching career after her own divorce, and she's

0:36.4

been in the trenches of doing this work long enough to have real perspective on how dating changes across different seasons of life.

0:43.0

We get into what it's actually like to start dating again after a long marriage, how the pool shifts when you get into your 40s, 50s, and 60s, and what to do with the jadedness that builds up after enough disappointing experiences,

0:56.0

which I know is relevant to you even if you're not later on in life, right?

1:00.5

If you're 20s, 30s, you also have jadedness sometimes.

1:04.3

We also talk about how to stay open to someone's story without immediately writing them off

1:08.3

for their baggage.

1:09.6

And Sandy also talks about navigating dating as a single parent,

1:12.6

all about the conversation to have with your kids before you start,

1:15.8

when to introduce someone you're seeing,

1:17.7

and how to get creative with scheduling when your time is limited.

1:21.4

Plus, she shares something she did with her dating profile

1:23.9

that I really hadn't heard before, and it got her some dates.

1:27.0

At the end,

1:27.8

we answer a dating dilemma from someone who is in a no strings attached situation and she's not

1:32.3

sure if she should walk away or stick it out. As always, I love hearing from you. You can

...

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