Second Time Around? Why Dating After 40 Is Better Than Your 20s
Entering or reentering dating in middle age is daunting for all kinds of reasons (as I very much know first hand).
All the time I hear people saying “I’m too old for this.”
But — and I mean this from the bottom of my heart — dating in your 40s and beyond is so much better than dating in your 20s and 30s.
Dating then had its moments, for sure — but let’s not romanticize it. Remember the messiness, the confusion, the anxiety it caused?
If you’re needing a little dating pick-me-up, here’s a reminder of why dating at your age NOW is actually an upgrade.
- You Have Your Own Place (and It’s Peaceful)
No roommates, no awkward run-ins in the hallway, no “Can you keep it down?” from behind a thin wall. Now, your home reflects you — and it’s a calm, private space to connect with someone (or just decompress after a weird date).
- The Wine Is Better
You’ve graduated from whatever was on sale to something you actually enjoy. Sharing a glass of good wine now complements meaningful conversations, not just serves as a social lubricant.
- You Know What You Don’t Want
In your 20s, you might’ve swiped or said yes just to see where things went. These days, you’re clear on your dealbreakers, your non-negotiables, and your worth. That kind of clarity is powerful — and efficient.
- You’re Comfortable in Your Skin
You’re not performing, you’re not second-guessing. You show up as you are, and that makes dating feel more grounded — and a lot less exhausting.
- You’re More Intentional
It’s no longer about filling time or seeing what sticks. You’re looking for something real — and you’re much better equipped to spot it when it comes along.
Bottom line? Dating after 40 isn’t about trying to recreate your youth. It’s about moving forward with more self-awareness, better boundaries, and a stronger sense of what actually makes you happy. No need to rush — you’ve done this before. Now you can do it better.
Happy dating,
Alyssa
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Hi! I’m Alyssa Dineen and I’m a personal stylist and dating coach all rolled into one. I started Style My Profile to help other online daters feel better about getting out there— and staying out there— in the world of online dating. Whether it’s to meet your soulmate, to find a fun person to have dinner with or even just match with more people, I can help you from the ground up.
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DIY PROFILE KIT
Purchase our DIY Profile Kit, designed for getting your profile swipe-right ready in as little time as possible.
$79