9 Common Senior Dating Mistakes (Online & Offline)

Senior Dating

9 Common Senior Dating Mistakes (Online & Offline)

April Braswell April Braswell
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If you ask, most senior singles will tell you that looking for love is very different today than it was when they were in their 20s and 30s. Not only are there different processes, but online dating has thrown a lot of people a curveball.

To help you navigate this new dating scene, I’ve compiled a list of nine common mistakes midlife singles should try to avoid.

1. Neglecting to Tap Into Online Dating

While online dating started becoming more mainstream all the way back when Meg Ryan met Tom Hanks in “You’ve Got Mail,” there are people who still aren’t tapping into this resource, especially those among the over-55 population.

If you’re one of those people, the time has never been better to sign up for a dating site or app. We’ve written a ton of articles and reviews specifically for seniors to find the best platform for them.

Photo of a heart on a laptop

Online dating is the best way to meet a lot of people quickly.

I recommend starting with one site to get your sea legs, and then add another site or two to maximize your chances of finding a mature life partner.

2. You Have a Stale Dating Profile

If you’re using photos from more than 10 years ago, you’re guilty of having a stale dating profile. I’ve seen too many midlife singles put up a profile on a dating site, and then they just leave it there for months without regularly updating it.

Photo of a man looking at a dating profile

Updating your profile every few months or so will put you at the top of results.

If it’s been four to six months and you’re still using the same photos and information, it’s time to switch things up. Think of the hobbies you enjoy doing, and then put up a recent photo of you doing that. Or maybe you’ve seen a new movie or read a new book — that’s worth mentioning!

3. Relying On What Friends Say About You

Too many mature singles use phrases like “My friends tell me I’m…” in their dating profiles. By now, you should know what your best attributes and characteristics are.

Socrates said “Know thyself.” Potential dates — and you yourself — expect people on dating sites to be able to authoritatively portray who they are.

Photo of a group of seniors

Try to describe yourself online without saying things like “My friends tell me I’m…”

Read some articles about how to write a dating profile, or hire a professional to do it for you. Don’t fall back on clichés, or you risk getting swiped on.

Caveat: If you’re a recent widow or widower over 80, I’d say you’re allowed to say things like “My grandkids tell me I’m…” in your dating profile. From you, that can be charming.

4. You’re Too Passive Online

Oftentimes, senior singles will post a dating profile and try to skirt having to pay the membership fees by waiting until someone approaches them. And then, only because they have to, will they shell out some money. Online dating doesn’t optimally work that way. If every senior single is passive, how will any of you ever meet for a date?

Photo of a man relaxing with a laptop

If everyone were passive online, no one would get a date.

Online dating works best if you’re proactive. First, approach prospective dates with a good opening line. Then follow up with them regularly with the goal being to get to the first date within a short time frame.

5. Using Too Many Filters

Online dating isn’t the same as working with a matchmaker who gets to know you and has a Rolodex of singles in your age bracket. In fact, matchmakers are typically more challenged to keep that stable full of quality senior men and women.

Photo of a woman doing thumbs down

Don’t go overboard with the profile filters on dating sites.

The goal of online dating is to get to the first date. The goal isn’t to use every profile filter you can to meet “The One.” Yes, you should aim for quality dates, but don’t waste your time and energy by filtering profiles so much that you never even get to a first date. If you’ve been on less than one date a month, then you may be guilty of doing this.

6. You Meet for Dinner for the First Date

In my coaching practice, I see that some senior singles feel pressured to go out for dinner on a first date. In my opinion, a dinner date just adds financial pressure to the tension that’s already there.

It’s a significant investment of you and your date’s time when really you just need to meet to vet for in-person chemistry and good conversation. Leave dinner dates and serious conversation for a second or third date. My advice for a first date is to meet for coffee in the early evening at a lovely cafe or restaurant with a view.

Photo of a coffee date

Coffee dates will put less pressure on both of you.

By lowering the bar for the first date, you’re more likely to go on more dates, meet more people, and build your dating confidence.

7. Saying “No” Too Much

This is a pattern that many people fall into, particularly widows and widowers. They have an idea in their minds of a perfect mate who must look and act like their former partner, so they say no to a lot of dates or even non-romantic group activities.

Photo of a man wagging his finger

Saying yes to as many things in life as you can will open a lot of doors.

It’s better to say yes to life and get back out there, so you can practice your social and flirting skills. Do some quality grief work, and then aim to date again. Try to have some different aspirations about the kind of life companion you seek now. Maybe you don’t want to remarry, but sharing life and intimacy with someone would be great wouldn’t it?

8. You Let Appearances Fall by the Wayside

Yes, ladies and gentlemen, you’re no longer 20, an age when you probably didn’t have to do much with your hair, makeup, or clothes. It’s OK not to be that into appearances, but try to do a little something before each date.

Even a small gesture, like putting on mascara or trimming your beard, will signal to people that you care about taking care of yourself. As Joan Rivers used to wryly remind us, “Put on some lipstick. It wouldn’t kill you to wear a pair of heels.”

Photo of a man with a hole in his sock

You don’t have to wear ties or heels on first dates, but put in some effort.

Some single men and women over 50 have confessed to me: “April, I’m lazy now. I don’t want to have to wear a tie (or heels) on a date anymore.” I’ve written about this in the past, but now that Casual Friday is very common in corporate life, many men and women are no longer in the habit of wearing ties or heels daily, let alone for a date.

Those who do don a tie or heels for a date are people after my own heart, but honestly you no longer have to wear these items. However, you still need to spiff up a bit. Men, maybe wear a blazer or a sports coat. Women, you can wear some nice flats. Basically, the point is to show your date that you’re there to impress him or her.

9. Doing a Bucket-List Item for a First Date

A first date isn’t the time to go skydiving like couples do on some TV shows. Instead, aim to put each other at ease. Even if you live a more adventurous lifestyle and seek a mature mate who would share some of that with you, you’ll have a chance to share those interests at another time.

Photo of a senior skydiving

Don’t use first dates as an opportunity to check things off your bucket list.

I think a second date can be a good time to show off your vitality for life. You can rent bicycles and have a nice ride in your downtown area, and then you can have a nice meal at a midprice-range restaurant.

When You’re Proactive and Open-Minded, You Can Easily Find the Love You Want

Decades ago, senior singles were depicted by society and Hollywood as being romantically retired, but that’s not true. Midlifers expect and actively seek a romantic life — just at a different pace than their younger counterparts.

Whatever relationship you’re looking for at midlife, when you’re proactive and keep an open mind and open heart, you really can find the love you seek.