Dating is awkward at any age, but when you're over 50 there are a whole new set of challenges facing you. Daunting as it may seem, dating is still fun, and love is still out there.

1. The ex factor

old 1980s wedding
via Lindsay Basson / Shutterstock.com 

With the average age for divorce set at 44 for men and 42 for women, it's no surprise that dating is on the rise among people entering into their 50s. But this so-called 'baggage' can be one of the biggest issues of dating at middle-age—no one escapes the big ex.

Whether divorced, widowed, or never married in the first place, it's likely that the significant ex has left an impact. That may be in the form of children, which can be the most rewarding thing to come out of any relationship, or emotional damage, which can be inevitable. The first step to getting back into dating is accepting this baggage, both your own, and that of others. 

Stella Grey (pseudonym), is 50-something and writes of her dating experiences in her fantastic Guardian column Mid-Life Ex Wife. The following comes from an email exchange with 40-something James, he admires her lack of ex speak compared to others:

 

"I have my baggage, believe me, I told him, and it’s unrealistic to expect people who have lived half a century to be able to discard the past completely. But that’s exactly what we need to do, he said. That’s why I left my wife. (No, I won’t be meeting James. Not even to slap him.)"

 

Accepting the past as the past is a huge step towards a positive future. Everyone has an ex or two out there, but that shouldn't stop anyone re-entering the dating game. Use your experiences with your ex to figure out what you want from the future. 

 

2. I've met everyone I'm ever going to meet

Friends forever
via Internetkhole

As we get older, it seems that our friendship circles dwindle. Remember in school how easy it was to make friends? University years, early working years, friendship circles were endless, and it seemed like every outing brought about a new acquaintance. 

Why do friendship groups dwindle? The day-to-day grind gets in the way, most of us settle down and get into relationships which unfortunately means friendships are put on the backburner. Just because we get older doesn't mean we become less social, it may just require a little more effort. Reaching out to friends as we get older is also beneficial to health.

Irene S. Levine, PhD, the self-declared 'Friendship Doctor', has the following to say on the matter. 

 

"Making friends is more a function of circumstances rather than age, per se. No one is more attractive to others than someone who is engaged in life. Find something that stirs your passions and places you in regular contact with the same people week after week. Friendships will follow."

 

The modern technological age has made it easier to reconnect with old friends through social media. It's also made it easier to find events that interest us, where we're likely to meet like-minded people, and who knows who you may meet from there.

 

3. Using technology to get back in the game

At least dating will never be as awkward as these 80's dating videos

Alright, it isn't the old-fashioned way, but it is the modern way. There was a time when online dating was something to be embarrassed by, but nowadays a third of relationships start online. With the speed at which people are signing up to these sites, it is predicted that by 2040, 70% of all couples will have met online.

Dating websites are by no means a new concept, but there have been many advances. Websites are now more specialised you can date people over 50 only, or find music lovers, book lovers, or go even more niche and find people with similar kinks (eep!). Paula Hall, a relationship counsellor at Relate says this of online dating:

 

"Couples are more likely to be on a level playing field and share the same agenda. Any relationship that forms is more likely to be based on a shared value system, the same interests, the same legwork as opposed to a relationship based on chemistry alone, which, as we all know, is the quality that tends to fade first in a relationship."

 

Most dating websites use algorithms—sort of like a secret recipe—to match people. How these websites measure compatibility differs from site to site, most apps use location settings, whereas websites tend to use personality tests and interests.  

When it comes to dating sites, it's often worth paying for a service. Yes, it's cruel that big business is exploiting lonely hearts, but there is a level of psychology involved. According to tech magazine Wired, "When a subscription is involved people are more keen to progress offline to actual dates and abusive messages are at a minimum." 

Technology only serves to broaden the pool of what's out there, so why not dip your feet in and find out if it's right for you?

 

4. New dating challenges

Answering machines

When was the last time you remember going on a date? For many over-50s that can be as long ago as 20, 30 years. Now that's daunting! It may be alarming to hear that the over-50s share a lot of the same dating challenges as back in the day, but with one huge benefit: you know yourself loads better now.

 

"The combination of middle age and new technologies that feels so scary and doom-laden. Yes, there is wisdom, experience and a different kind of hard-won confidence, but there is baggage, too."

 

Candida Crewe turned 50 in 2014, and told the Guardian of her new dating anxieties. Baggage is a huge concern. On the one hand, there is getting out there and having fun (like you did in your teenage years and twenties), but there are a whole new set of things to take into consideration:

  • Younger children: once they've fled the nest it's a lot easier to fit dating in and approach it more casually. But when they're a bit younger it may be harder to know what to tell the kids, let alone take risks. 
     
  • Technology: When you were younger it may have been the anxiety of a missed call and the lack of an answering machine to pick up the message. At least in the 90s the introduction of '1471' eased that anxiety a little.

    Now it's all texting, emails, dating apps, and if you're lucky (or unlucky depending on your POV) 'sexting'. Welcome to the era of "But what if they don't text back?" and "what does 'that' mean?" and those with Whatsapp need to beware the dreaded 'd*** pic', which according to Stella Grey is as much a thing in your 50s as it is in your 20s.
     

  • Jealousy: We're not talking about dating jealousy either—that's certainly not a new challenge. The face of dating has changed so much in the past 20 years that your married friends will get curious and want to nose in at dating profiles, see how the apps work, and help you decipher those "what does 'that' mean?" texts. It can be fun, but it can also be a little bit annoying.
     
  • Exes: Yes it was number one on our list, but it makes a reappearance. Everyone's got 'em. This may unfortunately mean that there are more than a few damaged goods out there. The only way to overcome this is to accept the ex, but at the same time, assess how much drama you want in your life and how much drama this particular person's ex is going to cause.

The biggest challenge to dating at any age is understanding what you want. Just remember who you are and have fun.

 

5. First date nerves

First date nerves
via Internetkhole

Those first date nerves sure don't ease with age! As just discussed, a lot of those old issues from dating many moons ago reoccur. What will I wear? What will we talk about? Will it be awkward? Will I even like them? 

It's the same for everyone.

One Reddit user who hadn't dated in over 20 years put out a call for help on the message boards,"I am ready to date, but I feel so clueless and lost that I hardly know where to begin or what to expect. I spoke with my date on the phone and we agreed to go get dinner and drinks this Monday. The world has changed a lot in the last 20 years. I feel like an inmate stepping out into the world after a long sentence. It's exciting, but scary." Another user who had come out of a 16-year marriage had this to say:

 

"Good news: Dating is fun! It was super strange for a bit, but you will get your 'sea legs' back sooner than you think. Do not talk about divorce, do not talk about your ex."

 

There is no formula to a successful first date. Choose somewhere you both feel comfortable, and remember to have fun. It'll either go really well, or you'll get a great story out of it.

If we can learn anything from watching Channel Four's hit series First Dates, it's that the young 'uns in their late teens/early-twenties all seem to be having boring/awkward dates, while the senior daters aged 60 and beyond are having a hoot. Perhaps they find it easier to let go and be themselves.

 

6. The sex factor

Gone with the Wind Kiss
Still from Gone with the Wind 

If you've been in a relationship with one person for the last 10, 15, 20 years; or perhaps the sex in your previous relationship tailed off and you haven't had sex for a while; maybe you've been single for some time but haven't felt ready to get back in between the sheets, sex can seem daunting.

Great news for the over 50s, this age can be the most sexually satisfying. Blogging for the Huffington Post, Erica Jagger has this to say:

 

"At 50, dating for the first time in over two decades, I ventured into a brave new world of sex that was kinda like sex in my 20s, only a zillion times better."

 

Nudity is a common concern for this age group. Bodies change a lot, but that's no secret. It's likely your partner has the same concerns as you do and it's amazing how quickly this anxiety is out of the window to make way for pleasure.

Getting to know each other's bodies is always a challenge, especially for women. Men shouldn't feel inadequate if they can't bring a woman to climax first time around—everyone is different and it's all about learning what works and what doesn't. 

The great thing about sex in your 50s is that people are more confident, willing to try new things, and most importantly are more likely to communicate during sex. 

 

7. Is this the right person for me?

This question lingers through generations. If you have an ex, then it's a question you're no doubt already familiar with. There is only one way to find out, and that is to take a risk—the real question is: is that person worth the risk?

 

Ready to get back into the dating game? Sign up to Reader's Digest Dating, exclusively for the over 40s.

 

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