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7 Dos and 7 Don’ts for a First Date as an Older Adult

Getting back into the dating scene at 50+ can be scary. Here are tips to help you through it


spinner image unhappy couples on a date at a restaurant with a spotlight on a happy couple
Illustration: Pete Gamlen

Dating — and finding love — aren’t just for the young.

But dipping your toe back into the dating pond as an older adult can be overwhelming and downright scary sometimes. What do people talk about on dates now? Who pays? Should you bring up past relationships?

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If you’re nervous, don’t worry: We’ve got you covered. Here are tips on what to do, and definitely not do, when meeting someone for the first time.

What to do on a first date

1. Be upbeat and confident. It’s your attitude that will make or break your date, says dating coach Bela Gandhi, founder of the Smart Dating Academy in Chicago: “You have to adjust your mindset to eternal hope, saying love will come to me when, not if. There are a lot of fish in the sea; get excited.” Dressing to impress — yourself and your date — can help give you a confidence boost.

2. Consider your body language. Having a “welcoming presence” is important when meeting people for the first time, says matchmaker Tennesha Wood, founder of the Broom List, a service based in Atlanta that boasts an 85 percent match rate. Turn toward someone when speaking and look directly at the person, she suggests.

3. Be honest. Be truthful about your age and online profiles and photographs, Wood says. “The worst thing you can do [in] online dating is to be less than honest,” she adds. “It will come back to haunt you. It’s about diminishing the trust before it’s built.”

4. Come prepared. A conversation is a two-way street. “Have questions ready to ask the person to share their life, their dreams, and be ready to answer similar questions,” Gandhi says. “You’re trying to find common points of interest.” She adds that questions should be open-ended, such as what was the last book you read and where have you traveled, to prompt more than yes-or-no responses.

5. Keep first dates short. Gandhi suggests limiting your first few dates to about two hours, which is when the brain starts to focus on the negative more than the positive. Meet for coffee, lunch or an appetizer instead of a long dinner, she says.

6. Pick the proper venue. Dating experts advise planning an active first date, such as a walk through the park or a round of mini-golf. “It makes conversations easier because there may be a crazy squirrel or saxophonist that sparks a conversation,” Gandhi says.

Steve Holt, 66, an entrepreneur in Sandpoint, Idaho, likes to take a walk, grab a cup of coffee or share a glass of wine on a first date. “You want to have a date that makes room for conversation,” he adds. “Skiing, for example, you can’t really talk to each other.”

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7. Agree who pays at the beginning. People have differing opinions on who should pay for a first date — or maybe you'd rather split the bill. Prevent awkwardness when the check arrives (which also sets the tone for the end of the date) by agreeing on the payment terms before or at the very start of a date, advises the dating website eHarmony.

What to avoid on a first date

1. Don’t greet your date with a handshake. Hug instead, Gandhi suggests. “It shows that you’re warm and comfortable,” she says. “It’s not a business meeting.”

2. Don’t bring baggage. Avoid long conversations about your terrible divorce or grief over a partner’s passing, especially on a first date, Wood says. Don’t compare your dates to previous partners. On a personal level, “don’t use your past experience as a meter for the future,” she says.

3. Don’t create obstacles. Keep an open mind. Don’t limit yourself to only wanting to date tall people or people who live in the same city. “A person might not be exactly what you imagined, but if the values line up, be open to it,” Wood says. “It’s about giving people a chance.”

Tracey Altman of Wilmington, North Carolina, has learned to be open to new ideas in the several years she’s been dating since her 2016 divorce. “One guy took me skeet shooting,” says the 57-year-old. “I said, ‘I don’t really think that’s my cup of tea.’ But I loved it.”

4. Don’t get distracted. That means keeping your phone out of sight — and maybe even turned off. The dating service It’s Just Lunch says first dates should be considered “no phone zones.”

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“I never take my phone out on a date,” Altman says. “If someone is looking at their phone a lot on a date, then you already know they’re not into you.”

5. Don’t put yourself in unsafe situations. To protect yourself, don’t provide personal information, including your last name, until after the first date. Provide your own transportation and meet in a familiar public place for the first few dates, experts say. For protection, Gandhi suggests getting a Google Voice phone number just for dating, so your regular phone number isn’t revealed. Google provides this phone service to Google account customers to make calls via their computer or mobile app; when calling from the U.S., most Google Voice calls to the U.S. and Canada are free.

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6. Don’t worry if sparks don’t fly right away. In fact, Gandhi recommends a Zoom or Facetime video call before meeting someone new in person. “A video call is worth 10,000 words if a picture is worth 1,000 words,” she says. “You can develop amazing relationships over video. When you take away the physicality of things, you get back to old-school dating. You develop a different kind of intimacy, emotional intimacy.”

Relationships take time to develop. Go on a second and a third date to really get to know a person, Gandhi adds.

7. Be cautious about having sex right away. When you have sex immediately, Holt says, “the emotional connection kind of takes second place,” he says. He suggests getting to know someone and seeing if there is long-term potential before being intimate with them. “It’s harder to back away from a relationship when you’ve been intimate,” he adds.

While 31 percent of singles are comfortable having sex on the first three dates, 69 percent want to wait longer, according to the Singles in America report by online dating platform Match.

“As we age, dating is just a lot different,” Holt says. “We’re looking for different things. We’re looking for more long-term relations with people and not just out there to date for the sake of dating. We’re looking rather quickly to the future as to whether we want to be with this person or not.”​

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