Katie’s 5 Tips for Dating After 40

katie couric and john molner on the beach

Katie shares the five pieces of advice that helped her navigate the dating world after 40.

The prospect of dating can be daunting, especially if you’re not in your 20s anymore. But whether you’re joining the dating pool because you’ve lost a partner, you’ve gone through a divorce, or you just never settled down, dating in mid-life is the new normal, and nobody understands this better than Katie. After her late husband Jay passed, Katie eventually decided it was time to put herself out there again, and she learned some valuable lessons from her second time as a single woman. She shared five pieces of advice with us based on her first-hand experience, and you don’t have to look any further than Molner to see that these strategies paid off. Whether you’re looking for a casual fling or a long-term commitment, Katie’s advice will help you reframe dating not as an uncomfortable means to an end, but as a fun and exciting way to meet new people and broaden your horizons. 

Say Yes to Everyone

“The best piece of advice I have is to say yes to everybody! (Unless you don’t feel safe or have legitimate reason to believe they might not be trustworthy.) Being open-minded about dating is crucial. When I was single, I had this mindset that I could learn something from everyone I went out with. Even if it wasn’t a love connection, it’s fascinating to meet new people, and everyone has something to offer. I think a lot of it is attitude. Don’t go into a first date with any expectations, other than that you’re hopefully going to meet someone interesting. Be open to going out with new and different people.”

Don’t Do Dinner

“A more pragmatic rule I have is to never have dinner on a first date. Always be careful — meet up in a public place — but instead of dinner, meet for coffee or a glass of wine instead. That way if it’s not clicking, even on a friendship level, you’re not going to be stuck sitting with this person for two hours, because those are two hours you’ll never get back. Although I asked Molner out for lunch for our first date, and he told me, ‘I don’t do lunch.’ So that went out the window.”

Enlist Your Entourage

“Don’t be shy about telling your friends that you’re interested in meeting someone. When someone says they might have someone to set you up with, stay on them about it — you might have to ask more than once. My friend Molly was the one who suggested I go out with Molner, and when she didn’t follow up, I could have just dropped it. Instead, I pursued it, so then she pursued it. Be persistent.”

Get Out of Your Comfort Zone 

“If I weren’t a public figure I probably would’ve been on all of the dating apps, but if you’re not having luck there then get out of your comfort zone and put yourself in a situation where you might meet someone new. Do something you normally wouldn’t do, like take a rock-climbing class, or go to an event at a museum, or join a club. If you stick to the same routine every day you’re never going to encounter new people, so this is a great way to meet someone you might never have crossed paths with otherwise.”

Be Inquisitive

“Learn how to be a great conversationalist. Don’t just talk about yourself the whole time, or wait for your turn to talk. Ask lots of questions, and really listen and engage with the person’s answers. People love to talk about themselves, and this can be a great way to find out unexpected and interesting elements about the person you’ve just met. It’s a good way to determine if this person has the qualities you’re looking for in a partner, but you also might learn something fascinating that you’ll take with you, even if you don’t end up going out again.”