4.4 • 3.6K Ratings
🗓️ 1 September 2025
⏱️ 25 minutes
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Casi wrote into “Ask Amy and T.J.” in their latest Yahoo relationship advice column, wondering if she should give a man 25 years older than her another try, now that she’s older and wiser. She met him when she was a freshman in college and he was in his 40s… Now she’s about to turn 40 herself and thinks they may be ready for love.
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0:00.0 | This is an I-Heart podcast. |
0:05.9 | Hey there, folks, it is Monday, September 1st, and age ain't nothing but a number when it comes to dating. |
0:15.4 | But what if she is an 18-year-old freshman? |
0:25.9 | Does age still matter if the gap is 25 years? But oh, the story gets oh, so much more complicated than that. And with that, welcome to this relationship edition |
0:30.1 | of Amy and TJ. We're going over Robes, a question that a reader sent into us on our Yahoooo.com column asking for some advice you can find |
0:40.2 | it yahoo.com a new one every week in the life section let's start with that rose there is an age |
0:46.8 | gap here 25 years now when you first hear that is big deal? Oh, that's a pretty big deal. |
0:55.2 | I mean, that's a parent to child generational gap. |
0:58.3 | Okay, so you would have a follow-up question immediately. |
1:00.4 | Hey, think about dating somebody. |
1:02.1 | He's 25 years older. |
1:03.8 | Your first question, you need to know how old the woman is right now, right? |
1:08.3 | Yes, 100%. |
1:09.4 | Because, well, there's already going to be literally a generation gap between the two of you. |
1:15.6 | But if you've lived enough life where you can go into that relationship with enough experience, |
1:24.2 | you won't obviously ever catch up with your partner, |
1:27.3 | but you've had enough life experience |
1:29.5 | that you can navigate your way through it potentially successfully. If you're young, |
1:34.9 | if you've just started off in life, if you've just left your parents home, it's like you just |
1:41.0 | went from your dad to your boyfriend. |
1:53.3 | Like it's almost as if you are still seeking that same sort of relationship where you've got that dynamic where someone is a parental figure to you because how could he not be? |
1:53.6 | Okay. |
... |
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