The Best vs. Worst Cities for Dating RANKED

Love Life With Matthew Hussey

Matthew Hussey

Relationships, 971900, Self-improvement, Education, Society & Culture

4.8 • 2.9K Ratings

🗓️ 12 November 2025

⏱️ 56 minutes

🔗️ Recording | iTunes | RSS

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Summary

Is love really easier to find in Chicago than in Los Angeles? Or is it all in how you show up? In this week’s all-new Love Life episode, we unpack the myths and realities of dating in different cities—and what your zip code might (or might not) have to do with your love life.

Plus, we tackle a Love Life Line question from a listener in her 50s who’s navigating the tricky waters of dating men who prefer much younger partners. Is this a red flag, or should she keep an open mind?

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Transcript

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0:00.0	Welcome everybody to Love Life. Today we talk about the best and worst cities in which to date and
0:12.9	try to find love. We answer a love lifeline question with a lovely woman who is in her 50s and
0:19.9	dating men who have been dating younger, far younger than
0:23.7	her, and wonders if she should see that as a turn-off or if she should still proceed with those men.
0:30.1	We respond to some comments from one of our recent podcasts that caused a little bit of a stir
0:35.2	among the audience. And we have a Steve's sleeves. So don't go
0:40.3	anywhere. It's all coming up in today's Love Life podcast. Enjoy.
0:49.5	Stephen, you have the data from Time Out on the worst cities in the world to date.
0:56.3	That's true. I do.
0:57.4	Take us through them.
0:58.9	Okay, you start with number one?
1:00.5	Are they in order of how bad they are, or are they just, these are ten horrible cities?
1:04.9	They're in order of how bad they are.
1:06.4	Okay, so number one's the worst?
1:08.1	The worst.
1:08.7	Let's start with number ten then.
1:10.3	Number ten, Vienna. Number's the worst. The worst. Let's start with number 10 then. Number 10, Vienna.
1:12.6	Number nine.
1:13.5	Wait, you have any comment on Vienna?
1:17.4	I haven't been to Vienna.
1:19.1	It's very small, I think, isn't it?
1:21.6	Small city.
	...

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