Aug 25, 2026 · 33 min · 12 segments
Whether you’re newly single, coming out of a long-term relationship, or you’ve simply been out of the dating world for years, getting back into dating can feel overwhelming. The apps have changed, the…
[upbeat music] So let's just start off by acknowledging how scary dating can be when you've had a long break or you're returning to it after a long relationship.
Some of the rules that existed when you were dating still apply today, like prioritizing your comfort, saying no to things that make you uncomfortable, and not chasing someone who doesn't like you back.
The core principles and much of what I talk about on this podcast apply to dating at any age no matter how you meet people.
And yeah, if you're coming out of a long relationship or marriage and you expect the people you're dating to be more mature because you're older and you're dating people closer to your age, I need you to get rid of that expectation because age doesn't have much to do with emotional maturity and communication ability unfortunately.
I used to ask, "How old are you, by the way?" And I would be shocked to hear that some of the behavior I expected from a high schooler or, like, someone in their early 20s would be coming from, like, people in their 50s.
Let's talk about the number one question that comes up when we're talking about getting back into dating, and that is, how do you know when you're ready? So first I wanna talk about what it even means to be, quote-unquote, "ready to date." It can mean three different things if you ask me.
One, are you ready to go on a single date? Two, are you ready to date and explore pot-potential relationships? Or three, are you ready to be in a relationship? If you're new to dating or coming back to it after a long break, I recommend just focusing on the first one.
[upbeat music] So let's just start off by acknowledging how scary dating can be when you've had a long break or you're returning to it after a long relationship.
Some of the rules that existed when you were dating still apply today, like prioritizing your comfort, saying no to things that make you uncomfortable, and not chasing someone who doesn't like you back.
The core principles and much of what I talk about on this podcast apply to dating at any age no matter how you meet people.
And yeah, if you're coming out of a long relationship or marriage and you expect the people you're dating to be more mature because you're older and you're dating people closer to your age, I need you to get rid of that expectation because age doesn't have much to do with emotional maturity and communication ability unfortunately.
I used to ask, "How old are you, by the way?" And I would be shocked to hear that some of the behavior I expected from a high schooler or, like, someone in their early 20s would be coming from, like, people in their 50s.
Let's talk about the number one question that comes up when we're talking about getting back into dating, and that is, how do you know when you're ready? So first I wanna talk about what it even means to be, quote-unquote, "ready to date." It can mean three different things if you ask me.
One, are you ready to go on a single date? Two, are you ready to date and explore pot-potential relationships? Or three, are you ready to be in a relationship? If you're new to dating or coming back to it after a long break, I recommend just focusing on the first one.
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