The Dreaded Second Date: Dating After 40 - Should You Stay or Should You Go?
When you're navigating dating after divorce, that moment at the end of a mediocre first date can feel like a crossroads. You've spent two hours with someone who checks the basic boxes but leaves you feeling... underwhelmed.
Dating After Divorce: The Lukewarm First Date Scenario
You walk into the restaurant and your date is there. He checks all the major boxes BUT…
He's dressed just a "teeny bit too casual" for your taste
You have good conversation, but he talks just a "teeny bit too much" about himself
He's nice and respectful, but is just a "teeny bit inattentive" to your experience
He answers your questions, but talks about his work and future in a way that wasn't interesting to you
You have an okay time, but you were sort of bored, didn't feel attracted, and don't really want to see him again.
And then on the way out, he asks for a second date.
Important Dating Questions to Ask Yourself
When faced with this situation, you have three options:
Option A: The People-Pleaser Path
Feel unsure, hesitate and then say, "Yes" because you don't want to be rude and don't know what else to say. Then go home and second-guess yourself because he's a nice guy and way better than all the other yahoos you've been swiping left on. Then you stew in self-doubt while vacillating between the decision to cancel or not, but afraid of being mean and called a flake. Then you decide to go on the date only to confirm yet again that you didn't want to be there.
Option B: The Contemplative Approach
Feel unsure and say, "I'm not sure. Is it okay if I think about it and let you know tomorrow?" Go home, connect with yourself and then send a text declining the second date.
Option C: The Authentic Response
Connect with how you really feel and say, "Thank you for spending time with me today, but no, thank you."
When Am I Ready to Date? Recognizing the Low-Effort Man
Part of knowing when you're truly ready to date after divorce is being able to recognize what you actually want - and having the confidence to act on it. That slightly underdressed, self-focused date might be what we call a "low-effort man" - someone who's not fully invested in making a genuine connection.
For divorced women over 40, your time is precious. Learning to trust your instincts isn't just about this one date - it's about setting the foundation for all your future dating experiences.
Which option would you choose? Let me know in the comments.