Overcoming fears and misconceptions of Online Dating for the 40+ Crowd

It is natural for humans to feel apprehensive about trying new things. Consider the first time you stepped onto a pickleball court, thinking, “This is so popular. What if I’m terrible at it?” However, chances are you didn’t let that stop you. You probably attended a clinic, learned the rules, had some fun, met new people, and realized that pickleball combines ping pong and tennis, and yes, it was enjoyable! Your anxiety disappeared, and a new passion was born.

As an online dating coach specializing in individuals aged 40+, I have had the fun and privilege of seeing my clients’ love lives for the past 30 years. I have helped set up over 33,000 dates, over 8,000 marriages, and countless relationships, and along the way, I have heard countless stories, excuses, fears, and frustrations.

Here’s what I frequently hear from frightened or misinformed daters—and why they are generally wrong. And they find this out fairly quickly.

The stigma associated with online dating

The self-talk generally goes something like this: “I must be desperate. How could my love life have come to this? The internet is full of scary men/women whose intentions are dishonest.” Truth: With the advent of online dating in the 90s came utter chaos—the internet, google, and dating sites were in their infancy. While it took about 20 years, many online sites and apps have done a good job setting up fail-safe procedures and verifications. And where did this get us? To a widely accepted method of dating.

There are good options for the over-40 crowd. A broad-based mega site like Match.com has a healthy population of singles and is a popular choice. But, it can be like looking for a needle in a haystack. Tip for Match.com: Always refine the filters immediately before you go live as this will eliminate about 90% of the population and drill down to what you are looking for. Now you have a manageable needle in an Easter basket. One more tip for efficiency: Ignore the Like section as anyone in the world can like you and go straight to the Search function. If you’d like a targeted age approach to dating, there are several options, and three sites that some have had success with: Bumble, Our Time and Silver Singles.

However, this will depend on where you live. For example, major markets will be well-populated (such as Chicago, Boston, Dallas, etc) but smaller markets (such as Boise, Fargo, Spokane, etc) will not have the volume that a mainstream dating site can provide.

Even Tinder and Hinge are now focusing on the 40+ age group.   Hint:  Always pay for their memberships and there are some tricks and tips to get ranked highly on these sites and show you to more people.  Yes, really!

You were married in your 20’s or 30’s pre-online dating

You may reminisce about the ease and naturalness of dating in your 20s or 30s before online dating became prevalent. You recall many potential partners you encountered through college, grad school, and the workplace, where face-to-face interactions were a daily occurrence.

Organic, right? Now, at the age of 46 or 63, divorced or widowed (or out of a long relationship) and with no prior experience in online dating, it is only natural to feel nervous about trying a new approach

1. Embarrassment: I don’t want my ex, my neighbor, or my colleagues at work to see me online. Two thoughts here: First, they are online doing the same thing. Second, you can control who sees you by actively allowing only a certain population to see you. This entails more work, but for the newbie may be worth it.

2. You are concerned about your “stack up” online against the competition. Two tips to alleviate this problem: First, hire a professional photographer to do your photos, with action shots. No one wants to see your LinkedIn headshot. Invest $2-300 and hire a service like SNAPPR which has a set Dating package–now you will have both current photos and well-done pictures. The first thing both men and women do online? Look at the photos. Second, hire a dating coach to write your profile. It is extremely challenging to write about yourself. A pro writer can make your profile unique, short, and stand out among the dating throngs.

3. Everyone brings baggage to the relationship

I don’t think of it this way. Everyone carries their own life experiences to the table. It’s all about perspective – these experiences shape who you are today. Dating after 40 may come with its own set of challenges like dealing with children and ex-spouses, but it’s also an opportunity to enrich your life with new experiences. Here are my recommendations: a) Don’t take a poll with friends and family before you leap into online dating. They know nothing! b) Never talk about your ex on the first few dates. It’s not relevant at this point why you got divorced or more about your widowed spouse–your only goal is do I want to go on a second, or third date with this person? c) Never, ever speak poorly of your ex or past relationships. It’s negative energy and what does it say about you? d.) If you have children under 18, don’t introduce them to anyone until it’s an exclusive relationship.

4. You are afraid of what people will think

Maybe you are frightened by the idea that friends or family may see you online and think you are a loser. (After all, they are online too, right?). From my perspective, that was a fear I saw among clients in the early 2000s, but now it has become a generally accepted method of dating. Family members, especially the “marrieds” seem to always like to ask singles about their dating and love life. A few easy answers I have found effective: “It’s great, there are so many interesting people I’ve been meeting” or “I’m having fun and I’ll let you know when I’ve met someone amazing.” Well, this efficiently and quickly shuts them down and leaves no space for negative energy or comments.

You have read many horror stories in the media about online dating.

You may be fearful of stalkers, gold diggers, or being taken advantage of. Of course, with hundreds of thousands of people online and over 1,400 dating sites and apps out in cyberspace, there will be some. Fortunately, it’s 2024 and while they have not been completely eradicated, they are more rare. I remember the Nigerian prince asking for money which was a big scam in its day. Or someone asking for money for a plane ticket to come visit you. The media has done a good job educating us on the pitfalls of online dating, but remember the media is also looking for sensationalist and unique stories. The exceptions. We are too well-educated with online dating now to fall for these types of scams and the online sites/apps have features in place to identify and remove these issues.

So, here are some ways to avoid being scammed:

● Don’t use a free dating app/service. You want people who want a relationship,

and scammers are more likely to hang out on these types of sites.

● Do not contact anyone who only posted one photo.

● Your potential date keeps putting off meeting in person. Read this article by the

● A person asks for more information about you. This is a big red flag as they may be assessing the best way to contact you.

● If they have misspellings or odd language in their profile, it was most likely written by a bot.

These are good warning signs to be aware of, but don’t let this put you off online dating as it still has the largest pool of eligible singles and most are honest.

5. Online dating is visual

And, yes, this makes the average person nervous. The fear of rejection on looks alone is normal. I’m a big advocate of vetting my clients’ photos and I end up sending about 60% of my clients to a professional photographer who specializes in online dating photos. Yes, there are these photographers and I’ve found them to be very good. I am not advocating misrepresenting yourself by photo editing and erasing lines around the eyes, etc.–but you must have current photos as you want to show up on your date looking how you currently look. You want to put your best foot forward!

Some good rules to follow:

1. Do a wardrobe update before you start dating. I have had success with my clients using Nordstrom personal shoppers (they are free!). Two or three new looks will suffice and tell the PS why you are shopping for new clothes!

2. Hair/Beards etc: It’s time for an update on your haircut and possibly color. For men, the biggest complaint I get is unattractive facial hair. You want to look well-groomed in your photos.

3. The magic number of photos to post? Six. A headshot, full body shot, active shots (hiking, pickleball, horseback riding, skiing, painting, etc.), one shot with others (it shows you have friends), and perhaps a few travel shots.

4. The photos must be from within the last 18 months.

5. Adorable grandchildren? Or children under 18. Don’t post these.

Your confidence will soar with your new updated look and both men and women find confidence very sexy!

The worst dates: You show up and he is at least 10 years older than his photos plus 15 pounds!

 A little more on photos: Fun, action shots do well online. Photos where you are engaged in your interests: on the golf course, walking your dog, juggling (yes, I had a 60-year-old Wall Street man doing this and it garnered much interest), cycling, gardening, visiting a museum, bowling, celebrating a holiday with others. What won’t do well: LinkedIn shots, glamour shots, bathroom shots, and holding a fish.

6. Most of your friends are married, but they just don’t understand your situation!

How many times have you heard them say, “I know this amazing guy who would be perfect for you? You don’t need to resort to online dating.” And how often does that setup happen? The truth is, when it comes to dating, your married friends are not the best advisors. And even your single friends can be unhelpful if they have a negative mindset. It’s best to keep your own counsel until you’re ready to surprise your married friends by bringing your new “friend” to a dinner party.

a. Approach this with a strategy much like you may have used in your professional life

b. Have a plan. Perhaps- I will commit to online dating for 3 months, devote 2 hours each week to searching and messaging people, and go on at least 3-4 first dates each month.

c. It may feel awkward at first but practice makes perfect.

d. Most likely before you stepped out on the pickleball court, you took a clinic. Same for the golf course. If you want to speed up the dating process and have support and accountability, hire a dating coach with at least 10 years of experience.

e. How to hire a dating coach? Watch this video.

7. There is a common perception that online dating is only for the younger crowd.

However, this is no longer the case. According to Pew Research (an independent quality research firm), over 40% of people over age 40 are single.   There are numerous dating sites specifically designed for the 50+ age group, and choosing the right one is crucial for success. You want to be on a platform that caters to your demographic, has a strong presence in your geographical area, and offers a higher percentage of potential matches of the opposite sex.

According to Pew Research, about a quarter of those in their 40s (23%) say they have used online dating platforms, with this number continuing to grow.   Don’t discount online dating:  Pew also reported 1 in 3 marriages in 2023 occurred meeting online.

Personally, I have found more traction in the past 5 years with 50-70-year-olds using online dating, looking for a long-term relationship. It’s become much more widely acceptable.

However, you need to be on the right dating site/app for your demographic and geographic area. In general, while I do much research for each client before choosing one, I find broad- based dating sites such as Match, Bumble, Hinge and Silver Singles to be safe bets. They have volume and easy customer interfaces as well for the more tech-challenged user.

I have a 56-year-old client who is an executive at Google in California who was unhappy with online dating when he came to me. A friend in NYC had recommended Coffee Meets Bagel.

 While this may be a strong choice for the East Coast, its membership is very small out West. Once on the right site, he began meeting quality women. For him, Bumble was the right choice.

Finally, the most common phrase I come across? Men say, “All the great women are already in relationships.” Women say, “All the amazing men are already married.” I can’t help but laugh and reflect on the frequent calls I receive from my clients who have found their special someone. I think I have the most incredible job in the world.

Dating and love have been my life since I was in my 20s.

Author:   Andrea McGinty has helped singles find love for over 28 years. She is the founder of the iconic 33000Dates.com (current) and It’s Just Lunch Dating Services founded in the 1990s and later sold to private equity with over 100 locations globally. In the 2020s, she is a firm believer that the best way to meet people is through online dating using a professional dating coach and specializes in singles in their 40s- 70s! Over 65% of her clients are happy in long-term relationships.