Everything You Need to Know About Dating After 50

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Try online dating

Meeting people online is likely the biggest shift that’s happened since the last time you dated. But for most people over 50, "online dating is where it’s at,” says Schwartz, who recommends using sites that users have to pay for. “That means the company has their credit card, and if they are a bad actor in any way, you can tell the company, and they can bar them from the site,” she explains.

Laino recommends sites like eHarmony and Match.com. “In my opinion, there’s a higher percentage of finding a relationship versus somebody just kind of fishing for a one-night stand,” she says.

Schwartz recommends working on your online profile with a friend and having them “OK” your picture (which, by the way, should be recent-not from 20 years ago, says Laino).

And don't worry if it takes some time to get the hang of online dating. “My experience is that a lot of people who’ve been out of dating for that long-even 15 years or 10 years - have a little bit of a learning curve,” says Laino.

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But don’t completely give up on traditional tactics

Although online dating has become the go-to for most singles, it’s still important to not put all your eggs in one basket. “There should be a rotation of online and face-to-face meetings,” says Laino. “I never think it’s a good idea to just hang out in one area.”

Laino recommends having friends or family introduce you to potential matches, going to outings offered by work, and going to meet-up groups for things like hikes and book clubs to find people who share your interests. “I think that’s actually a really good use of both online and in person, and it takes away the concept of a date,” Laino says.

If those methods don’t work, you can also try a matchmaking service, says Laino. Although they can get expensive, these services offer a more personalised experience, so you’re more likely to get a strong match right out of the gate. “You’re not just fishing online; you’re actually having someone narrow down a potential mate or two for you,” says Laino.

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Realise you’re going to get rejected

If you haven’t experienced dating rejection in a while, this can be discouraging at best and hurtful at worst. The key here is to not take the rejection personally, as it more than likely has nothing to do with you.

“People reject people for a whole host of different reasons,” says Laino. “Sometimes it’s because they don’t have the nerve to say hey, I’m dating a couple other people. Or hey, you remind me of someone. Or hey, I just feel a friendship vibe from you. So they end up just kind of disappearing, and it really comes off as harsh rejection.”

If you’re struggling with rejection, Schwartz says to keep in mind what she calls her "pineapple theory," which goes like this: Someone doesn’t like pineapple, so they take it off their plate when it’s served. But there are tonnes of people out there who love pineapple. “It’s the same fruit, but for no big reason except for individual taste, it’s a favourite of some and disliked by others,” says Schwartz. “But the pineapple is what it is - neither desirable or undesirable by nature. It just needs to find a pineapple lover.”

The same goes for you, too. So the next time you're dealing with rejection, remember: “You just need to find the person who has a taste for you,” says Schwartz.

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Don’t give up just because you’ve had a few bad dates

If you’re dealing with dating frustration, keep in mind that trying to find a partner is rarely a pretty, seamless process. “You may not find the love of your life on the first or second or third date, and that’s okay,” says Laino. “Dating is definitely one of those things that has lots of ups and downs.”

Recognise that you’re probably going to have to go on several dates with different people before finding someone you really connect with. That’s normal, so although it’s easier said than done, try not to give up after a few bad dates. “It could take a year or more to find the right person, but if you are determined, you will find them,” says Schwartz.

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Leave your baggage at the door

We all have insecurities and baggage from our past - from failed relationships to health issues or problems with your children. But to get back into the dating world, you need to be willing to leave your baggage behind and not let it keep you from finding future happiness with someone.

“‘People think: Well gosh, I’ve been divorced twice. I’ve got three kids. Who’s going to want me?’" says Laino. "But the baggage has to go out the door because the reality is, everybody has baggage.”

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Have a general idea of what you want

This goes for everyone dating over 50, but especially for those who’ve recently left a long-term relationship. “If they’ve been married before or they’ve been in a long-term relationship and now they’re coming back out into the dating world, I view that as almost a time of coalescence - a time of growth,” says Laino.

Before heading back into the dating scene, reflect on what in your past relationship didn’t work, and how you can avoid a partner with those attributes going forward. Your vision of what you want shouldn’t be a laundry list of qualities, but rather, a few core attributes that are important to what you feel makes up a healthy relationship.

“Look for core similarities, and think about what differences actually don’t matter,” says Schwartz. “For example, if you are not raising children, maybe religion or religious practices are something you can ignore or practice separately.”

It’s also important to not get caught up in too specific of an idea of what you want or fall into a pattern of looking for the same thing you were looking for in your 20s. “Reconsider what the right match is,” says Schwartz. For example, it might have been important to you in your earlier years that your partner have a prestigious job or make a lot of money. But now, you might be financially stable enough to not view that as a requirement from a partner. Be open to these new changes in what you’re after.

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Keep first date conversation light

First dates can be nerve-wracking, especially if you haven’t been on one in a few decades. Laino's advice? “Keep the conversation light and fun,” she says. “Don’t go heavy on what your ex did to you.” This same rule goes for body language. Make sure you smile often, and sit up tall and with your head up to show that you're happy to be spending time with this person.

Another topic you should try to avoid, or at least limit, is your kids. “The last thing you want to do is be having dinner with somebody and the conversation is all about the kids,” says Laino. “That’s not going to do anything for a spark.”

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Give a potential new partner three dates

It takes time to get to know someone so give it at least three dates to see if you click. “If you set up a vision and you go out on three dates and you’re questioning whether this person’s a good listener, or they acknowledge you, or whatever, and you haven’t seen it after three dates, then you’re probably not going to see it,” says Laino.

Another good rule of thumb? For that first date, keep it to a 20-minute coffee date, especially if it’s someone you met online. “That's enough for the first introduction, and it can feel very long for the wrong person,” says Schwartz.

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Only have sex if you’re ready (and be safe if you do)

At some point, dating will likely lead to sex, but remember: there's no need to rush it.

“I think the number one rule is do not have sex because you feel like you should have sex,” says Laino. “You have sex because you’re really ready. You feel comfortable with the person, like they’re not going to judge you.”

Be upfront with your partner about your feelings toward sex and what you’re comfortable or uncomfortable with. Open up the conversation to let them know if you’re nervous or haven’t had sex in awhile, says Laino, and ask them if you can take it slow.

“If you have some trust for the person, that should be a really great conversation and not an issue at all,” she says. And when you are ready to have sex, make sure you use protection. “Just because you’re older and not worried about pregnancy that doesn’t mean you can forget about condoms,” says Schwartz. “You can still get a sexually transmitted infection or disease.”

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Don’t give in to playing games

Remember how in your 20s you would sit by the phone and wait for that guy to call you and ask you out on a second date? If you’re over 50, you shouldn’t put up with that.

“I think at that age, at 50ish give or take, if somebody says they’re going to call you and they don’t, the end,” says Laino. “Get out of the game playing.”

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Pay attention to his life as a whole - not just how “perfect” he is

If you’ve found the perfect guy - he’s charming, sweet, sexy, and smart - don’t let those rose-coloured glasses keep you from still getting the full picture of his life and how you would fit into it. This is especially true when it comes to his finances, friends, and family.

“At age 50, he should have at least a comfortable lifestyle that shows responsibility,” says Schwartz. “Don’t make excuses for him just because he is charming, sexy, or compelling. Take a hard look at his spending habits. Are any of them scary? If you would consider getting married, would a joint economic status put you in jeopardy?”

Also keep in mind that when you start dating someone more seriously, it’s not just about the guy; it’s also about you creating an additional social group when you meet his friends and family and seeing how you fit into that, says Schwartz.

One key component here? How long it takes him to introduce you to the important people in his life. “Don’t let it go on too long without meeting his friends and family,” says Schwartz. “If he doesn’t include them he is either a) not serious, or b) hiding something.”

So whether you’re just getting back into the dating game or have been dating for awhile with little luck, just remember: what you’re looking for is out there. It just takes time (and a little effort) to find it. “There are plenty of people who will love you for who you are,” says Schwartz. “Don’t compromise on important values because of a weak ego.”