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How to Start Dating:  Advice to Connect after 50

By Nicole Pajer AARP Article published May 9 2024


Dating in your 50s and beyond is oh-so-much different than in your 20s, 30s and even 40s.

First of all, there’s a whole lot more “It’s complicated” when dating as an older adult. One or both of you may have gone through a divorce, are supporting grown children or grandchildren, or are a caretaker for parents.

Priorities are likely different than they were in the past. For instance, you’re probably not shopping for a partner who will make good parent material. Maybe you’ve learned to love me time and don’t need someone with you 24/7.

But how do you connect with someone at this age? If you notice someone you’re interested in, how do you approach them? We tapped some dating experts who shared their best tips.

How to meet someone new


Stand out onlinePew Research found that 2 in 6 adults over 50 have tried online dating in some capacity. To really find the benefit, try spending at least three months on a site, says Andrea McGinty, an online dating coach and founder of 33000Dates.

“Many people want to quit after two weeks — but do not quit, as it will make sense once you get the practice using the site/app,” she says.

She suggests registering on a site that works best for you — not just going with one that your friend used. “Don’t pick a site because your best friend in New York chose it and met her boyfriend. You may live in Chicago or Dallas, and the same site can be very different in various parts of the country and not have the same quality of subscribers,” McGinty explains.

If you’re intimidated by filling out a profile, ask for help — either by running it by a friend whose writing skills you admire or hiring a professional writer to assist you — and yes, there are professionals who specialize in writing people’s dating profiles. “Think of it this way: Before you played golf, you probably had a few lessons. Same with pickleball. Get a pro to write your dating profile, vet your photos, assist with site selection and help you write unique messages. It will save you 80 percent of your time, and you won’t feel like you have a full-time job,” McGinty says.


Head to singles scenes — for your age group. Putting yourself in an environment for singles of a similar age is a great way to meet people who are in the same phase of life as you.

You don’t have to work so hard to ask someone out because everyone is there with the same agenda, says Pepper Schwartz, a relationship expert on Married at First Sight and author of Dating After 50 for Dummies. All you have to do is smile brightly and see who returns your gaze. Then strike up a conversation.

“There’s a place in Palm Springs [California] called the Nest, which is well known for over-50 pickups. So in a place like that, you don’t have to say much, because if you’re there after 9 or 10 o’clock, that’s what you’re there for,” Schwartz says.

Find a similar spot in your town to mingle with other singles — or check out social media, your community center or a website such as to see if there are any singles mixers you can sign up for.


Parties are a great way to meet people, as everyone invited knows other people invited in some capacity — the host at least. This makes it less likely that you’re meeting a stranger, which can be more awkward to navigate.

Schwartz says a great conversation starter in these situations can be to ask, “Hi, I’m so-and-so, how do you know so-and-so?”

Scan the room wherever you are. When you’re out and about, pay attention to who is around you. If you’re at a sporting event, see if someone interesting is seated near you. Or maybe you’re at the airport and notice someone you’d like to talk to waiting near you to board the same plane. “I have a very close friend who was in a line to get on an American Airlines flight and started talking to the guy behind her. And they’re married today and have children. So no opportunity should be seen as not an opportunity,” Schwartz says.


You have someone’s attention. What now?

Start a quality conversation. Once you see someone you may be interested in, the first move to make, Schwartz says, is to try to strike up a conversation.

Ideally, you want to move away from a quick compliment — “I like your shirt” can easily be met with a quick “yes,” then fizzle — to something that will get people talking.

After a nice chat, you can say, “Would you like to grab coffee sometime and continue this conversation?” If you ask someone out and they aren’t single, don’t panic, Schwartz says. Most people, if you ask respectfully enough, will take it as a sign of flattery.

Find common ground. When it comes to reaching out to a dating prospect online, try tossing in a dose of humor. “Pretend they are already friends, and write in that manner. No boring ‘Hi, how’s your weekend?’ or ‘Wow, you are so pretty’ — those messages just get ignored,” McGinty says.

Avoid certain topics. When it comes to conversations to avoid in an initial meeting, these are the top three: “Don’t talk about everything wrong with you. Don’t talk about health scares or health issues. Don’t talk about your grandchildren or your children,” she says. This helps to keep the focus on allowing the person to get to know you and keeps things light and fun.

Nicole Pajer writes about health for The New York Times, Woman’s Day and other publications.   Check her out at @NicolePajer on X


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