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The 8 Big Dating Mistakes of People Over 50

Dating and relationship experts weigh in on the biggest ways we self-sabotage

By Sara Schwartz

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Couple on a date

(This article appeared previously on

If you're single, over 50 and ready to mingle, you're hardly alone: There are millions of unmarried Americans age 50 and older. But are you sabotaging your own efforts at finding love in the dating pool?

We talked to dating and relationship experts all over the country to find out the most common dating mistakes people over 50 make. Here are the big eight:

1: Keeping People at Arm's Length

"My clients over 50 have often verbalized not wanting to look like an 'old fool' in a dating relationship," says Tarra Duford, a relationship specialist and CEO of Family Matters Counseling Group in Orlando, Fla. "Playing games and/or remaining aloof by not getting too involved may make you feel safe, but you run the risk of coming across as unfeeling, uninterested and detached."

Instead: Just keep telling yourself that people of all ages worry about looking foolish. "Being honest with your intentions, likes, dislikes and what you are looking for in a relationship will never lead you astray," says Duford. "Either you find what you are looking for or you find that the individual you are interested in is not the best fit for you. To receive love, one must be open and ready to accept it."

Couple on a date

2: Choosing a "Type" and Sticking With it

"The No. 1 mistake people over 50 make is continuing to go after their 'so-called type,' says Cindi Sansone-Braff, a.k.a. The Romance Whisperer,  author of Grant Me a Higher Love and Why Good People Can’t Leave Bad Relationships. "Ask yourself, 'How has going after my type worked so far?' If the answer is 'not so good,' then start thinking outside the box."

Instead: Try dating someone who simply seems like an interesting, kind, fun, successful human being, suggests Sansone-Braff. "By the time you’ve lived a half a century or more, you know it’s what’s inside that counts," she says. "Stop worrying if he’s cute, or how tall or short he is, or whether she has blonde hair and long legs. And, by all means, stop saying he or she isn’t your type before you’ve even given the person the chance to prove otherwise. You might just find out that when you let go of 'your type,' you actually let love in."

3: Not Dedicating Enough Time

Singles over 50 who are new to dating don't always know how much time dating can involve. By middle age, you may already have a full social life, a job and family demands, which means you may have to make some space for someone new.

Instead: Try to balance your life and create “we” time with your potential mate before you get too deep and blend families, says Julie Spira, CEO of, who has been coaching singles for over 20 years. "At the end of the day, your kids will grow up and have separate lives — and so will their kids. You both need to focus on your new relationship as something that could last for the rest of your life."

couple fighting
Getty Images

4: Interrogating Your Date

"How many children do you have?" “Do you own your own home?" “Are you on good terms with your ex?” If you find yourself conducting an interview the likes of which a police profiler would approve, take a step back.

"These questions are not good for those in the early phases of dating," says Duford. "Asking too many questions on a first date often puts the other person on the defensive. You can also come across as if you're filling your own personal criteria for what a mate should have, act like or look like." Not a great context for being authentic.

Instead: Focus the questions on interests, likes, dislikes and what they are looking for, she suggests. Use the beginning of a relationship to determine whether you actually like the person, and give your potential mate the space to be himself without the stress of living up to what they think you want.

5: Comparison Shopping

Over the course of your adult life, you've likely fallen in love with — or at least met — someone you consider to be the cream of the crop. But idealizing people in your past can cloud your present vision. "It’s hard not to compare someone new with the person you might still be holding a torch for," says Spira. "If you have a side-by-side checklist, there’s no way someone new will make the cut."

Instead: As Spira says, it's time to leave the baggage behind. "Knock your ex off the false pedestal you have him or her on — there’s a reason they are an ex," she says. "They weren’t perfect and neither will be the new person you’d like to start dating."

Man and woman relaxing together.

6: Not Being Honest and Upfront About Your Needs

While baring your soul can leave you feeling vulnerable, if you never ask for what you want, how will you ever get it?

"Pretending you really have no expectations or demands for the relationship, conveys you are happy with whatever course it may take," says Duford. "Engaging in ambiguous language and behavior puts you at a disadvantage when you are trying to get your needs met."

Instead: Express your intentions and answer all questions from a place of acceptance and understanding that there are no judgments, says Duford.

"When the question of 'what are you looking for in a relationship' comes up, you want to say something like, 'I am interested in dating with the possibility of a long-term committed relationship,'" she says, if your true purpose is finding someone you can share your future with. "You never know where a relationship will go, but you want to be clear and open about what you are interested in. Assertiveness should never be confused with being overbearing, bossy or demanding."

Woman thinking about sex life

7: Giving Up After a Couple of Bad Dates

According to a survey conducted in the United Kingdom, the average woman will kiss 15 men, go on seven dates, go on four disaster dates, have two long-term relationships, and have her heart broken twice. It's an emotional rollercoaster, to be sure, but one you must ride to find the one you want to be with. The trick is not getting discouraged by uncomfortable experiences, says Joan Price, sex expert and author of Naked at Our Age.

Instead: Price suggests looking at a bad date as:

  • A chance to practice dating: how to make an awkward conversation more pleasant, how much to reveal, how to elicit interesting info from our date (even if we never want to see that person again)
  • A good story to tell our friends
  • One step closer to the date that WILL work out!

8: Introducing Your Challenging Health or Money Issues Too Soon

If you have a chronic illness or are chronically struggling with your budget, these major life stressors are likely on your mind all the time. But avoid being too forthright, too fast, about your challenges when filling out an online dating profile or in person on your first couple dates, or they may end up defining you, says Trish McDermott, the founder of Encore Dating and former resident dating expert and spokesperson for

Instead: Lead with your strengths and the things you feel confident about, then let the hard stuff come up later. "These are issues that are best introduced after you have spent some time impressing someone with all your great qualities—kindness, sense of humor, passion for life, strong friendships, integrity etc," says McDermott.



Sara Schwartz Read More
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