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How to Start Dating: Advice to Connect After 50

Tips on finding people to date and what to talk about (and what not to) when you do

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Christine Rösch

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.

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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.

“You know more about what you want and not want in a relationship, and this shows,” says relationship coach Karina F. Daves.

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

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.

Say yes to social invitations (and not just dates). To meet people, you need to expand your social network. Schwartz recommends always saying yes, whether it’s a 70th birthday party, a retirement soiree or a Fourth of July BBQ.

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.

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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?”

Stand out online. Pew Research found that 1 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.

Keep in mind: If you go the online dating route, be alert to potential scams.

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.

Schwartz adds that in these instances, “you have to be your own wing person.” And it’s a good idea to take a quick glance at a person’s ring finger before you make your move to make sure they are not wearing a wedding ring; although that doesn’t necessarily tell you if they are in a relationship, it can be a great place to start.

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Dress to impress. When you’re out and about, wear an outfit that helps you feel your most confident. “Everything’s an opportunity,” Schwartz says. “I don’t care if you’re going even to the drugstore to pick up sleeping pills — go looking nice.”

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.

If you’re in line for a plane, Schwartz says to make a fun comment like “Here I am in another line. That seems to be my life lately. Waiting in lines for airplanes.” The other person, she says, will likely say, “Oh, do you travel a lot?” From there, the conversation has space to take off. Or you could be a bit playful and say something like “I like your shirt. My ex-husband had one just like it.” You could also say, “Where did you get your boots? I want to get my son a pair just like that.”

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.

Resist the urge to comment on someone’s looks. Though you may want to lead with “I like your eyes” or “boy, are you beautiful,” Schwartz says you’re better off finding common ground to talk about. Getting too flirtatious too fast can make someone feel uncomfortable, she says. “People — particularly over 50, 60, 70 — might come from a place where they haven’t been with anyone for a very long time. And they might be shocked or uncomfortable or even wonder, particularly with women to men, what the motivations here really are,” Schwartz says. Focus on being engaging, friendly and interested, she advises. And don’t be too pushy. If you ask them to give you their number or meet up a couple of times and they shut you down, take the hint.

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. Schwartz adds that it can be beneficial to find some aspect of a person’s profile that you click with and call that out in your debut message. For instance, if someone you are interested in pursuing writes about fly fishing and you genuinely are into that as well — send them a message and strike up a conversation about fishing.

Avoid certain topics. When it comes to conversations to avoid in an initial meeting, these are Schwartz’s 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.

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