5 Dating App Icebreakers for Older Adults

Your potential date could talk about the ’60s, and you could exchange stories about the flared jeans and go-go boots you wore to that high school dance. A mention of the ’70s could strike up a fun conversation about your favorite classic rock bands each of you has seen, or the fact that after college, your potential date took a year off to follow the Grateful Dead on the road. You may talk about the ’80s and all the big hair and bold clothing that were a part of your everyday life. This can give you an insight into what someone is passionate about and the activities they enjoy.

What is your greatest talent?

This question is a surefire way to get the conversation going and is actually deeper than you may think, as it reveals what the person really knows about themselves, says Audrey Hope, an addiction and trauma counselor in Brentwood, California. “This question breaks the ice because it gets the person to think about themselves, and they will appreciate that you are probing in this way,” she explains. People like to feel listened to, adds Hope, and this question allows them to really talk about themselves — whether they want to tell you that their greatest talent is helping strangers through organizing volunteer efforts or that it’s playing tennis and they love a competitive game.

It’s a gentle way to get someone to open up and can lead to topics that you can branch off into — like “How long have you been playing tennis? I play pickleball. Have you tried it?” or “I love volunteering too. Where do you volunteer? Have you ever worked at a soup kitchen? I was thinking of volunteering at my local one next Sunday.”

What is the most random fun fact you know?

You’ll likely be amazed at the stories that pop up when you ask this question, says Hannah Reeves, a licensed marriage and family therapist. “A client of mine tried this, and within minutes, they were laughing about trivia on historical oddities and old TV shows they both remembered,” says Reeves. This approach, she says, is a fun little window into someone’s experiences, tapping into all those details that only a few decades on this planet could offer. “The beautiful thing about this question? It’s almost guaranteed to get a laugh, or at least a raised eyebrow. You get a peek into how someone’s mind works. The weirder the fact, the better!” she says.

What are three things you would love to do on a first date, no matter how crazy?

When given the choice of coffee, drinks, dinner or any other activity, 43 percent of older adults chose coffee as their first date option, according to a 2022 study by DatingAdvice.com. But what if you could step outside of your dating comfort zone and do something with a date that’s a little more fun?

Asking this question prompts the other person to tell you what their ideal first date looks like, which makes for an interactive discussion about planning a first encounter that you would both enjoy. “This enables you to set up your date in a custom way, based on the blueprint and desires of the other person, giving a super-strong start to the relationship,” says Ice White, author of The Message Game: A Guide to Dating at the Touch of a Button. Even if your date doesn’t lead to a love connection, this can ensure you’ll still have some fun. And deciding among a concert, mini golf, a hot-air-balloon ride or an escape room, followed by dessert at a local fondue shop sounds like a fun conversation to have. This can also show if you align on interests or if you have little in common. For instance, if your date suggests an extreme activity like bungee jumping and you’d rather sit by the pool with a margarita, you two may not be the right fit.

If you could invite three people to dinner, dead or alive, whom would you pick?

“This one’s a classic, but classics are classics for a reason,” says Reeves. By finding out if someone is a history buff or just eager to chat with Jamie Lee Curtis, you’ll get a sense of whom they find fascinating. “Sometimes, I have my clients think about who they’d invite — it really shows off their values, interests or sense of humor,” says Reeves. “Plus, it can reveal if they’re more serious or just want to have a laugh.”

This also provides a jumping-off point for future conversations: “I love history and music too. I just read a great book about the Rolling Stones,” or “Idris Elba was great in that latest movie he did.”

Bonus: What was the last thing that made you laugh out loud?

This is a great way to get a good read on a person’s sense of humor, a quality many people rank high as being important to them in a partner. It can let you know if someone is sarcastic, dry, silly or playful — and whether your humor aligns. Discovering if you laugh at the same things (or if you aren’t even remotely on the same comedic level) may be an important factor in how well you bond; studies show that having a similar sense of humor can make you more drawn to someone.