Why You Probably Won’t Meet Someone with Online Dating

Ohhh, you are thinking, “Wow, Andrea, did you wake up negative? Wrong side of the bed?” No, just realistic.

This had been front and foremost in my mind this week as a dating coach – both from the perspective of listening to people’s rationalizations about OD (online dating) and potential clients who may want to use me as a coach – and their litany of excuses.

Ok, do you want the good news or the bad news? I’m going to start with the bad – and what I’ve been gathered this week based on conversations with intelligent people.

Here are four reasons why you most likely won’t benefit from online dating:

Your Photos Aren’t Doing You Any Favors – and You’re Not Willing to Change Them

Let’s be honest here. Online dating is a visual platform, and if you’re still using the same old photos from years ago, well, it’s like Einstein said: “The definition of insanity is doing the same thing over and over again and expecting different results.” Maybe your photos aren’t “really bad,” but they’re just average. In the world of online dating, you need to stand out.

Selfies and a bunch of random photos of you doing nothing won’t cut it. So, please take my advice and reach out to a professional photographer. Spend a couple of hundred dollars on professional shots. Trust me, it’ll make a huge difference.

I have a male client who’s quite attractive. He’s 68 years old, and I know this because we’ve had a Zoom call. But his photos are all selfies and don’t do him justice at all. I’ve been urging him to get professional shots, but he hasn’t done it yet. And guess what? It’s holding him back from finding great dating opportunities.

You Are Fast to Give Up

Did you know the majority of people quit online dating after 3 weeks due to frustration? Do you know you just quit before the magic could happen? Maybe you sent out 10 messages and got no replies? Maybe you looked at the people who liked you and said “never in this lifetime.” Well, you are doing something wrong. Let’s move on to what it may be.

You Send Out Boring Messages or Smileys

You spent money on a dating site/app. You invested time in a profile. You have photos. You answered all the questions on the app/site. Now you need to reach out to people and not think “the one” is coming knocking on your door.

Craft a well-thought-out message that stands out from the rest. Be unique, add a touch of quirkiness or flirtation, and tailor it to the person you’re interested in. Take a few moments to reflect on what you want to say and make it engaging. And don’t forget to end with an interesting or fun question based on what you’ve learned about them.

Yes, you must reach out with a message, not a heart, like or wink. It’s the 2020s – not the 1950s. I had a lovely 68-year-old woman tell me this week it was not proper for her to reach out and that men would think it forward. You know what men, which make up half of my clients, think when they get a like without a message? They roll their eyes and generally hit the Block Button. Why? You just threw the ball in their court and asked them to do all the work. It shows them also a lack of confidence on your part. And men find confidence sexy.

You Don’t Stop

Once you message someone, you need to wait for a reply. You don’t send numerous messages. One of two things will happen with this approach:

He Replies – and You Like the Reply

It’s time to make something happen. Otherwise, you are stuck in the pen pal loop of messaging with no date on the horizon.

So, you message back something specific: “Yes, I am interested – would you like to grab a drink late Saturday afternoon at Bistro 110 as it’s close to both of us, or I can do a coffee Sunday around 12pm – which works better for you?”

Now you are cranking – you’ve been specific about dates/times. Note: You did not say, “Let’s get together sometime.” Because, statistically, that will never, ever happen.

You Never Get a Reply

You wait a few days then hit delete. And, you don’t sit and wonder why he never replied, even after he “looked” at you online and viewed your profile. There is nothing wrong with you – you just move on. After all, there are dozens (if not more) of choices online.

And, please try not to take it personally when you don’t get a reply. I know what it is like – two years ago I dove into online dating myself, after a 24-year marriage and not dating for 5 years. (Yes, I guess a bit weird, considering what I’ve done professionally for almost 30 years – but you are ready to date when you are ready to date, right?)

There was this one man in Palm Beach I was sure was perfect for me. Well, I guess he didn’t think so as I never heard from him. And I wondered why for about 5 minutes, then said, “STOP wondering. Move on.” I met my husband-to-be on my 6th date. (Yes, every date I went on I reached out to the man first).

Ok, enough of what you are doing wrong and why online dating probably won’t work for you. On to the positive, good news.

Overall, 65% of my clients end up in long-term relationships – and that holds true for all age groups – from 50-somethings to 70-somethings.

So, Why Success for Some?


Attitude plays a crucial role. I rarely receive calls from people who are ecstatic about online dating and its wonders. Most of the time, individuals reach out to me when they feel lost and unsure about where to begin. They might be frustrated with their previous attempts or simply seeking an efficient and effective strategy.

Wondering why I conduct a 15-minute call with potential clients? Well, it helps me gauge their attitude and coachability. During these conversations, I often find that most people are hopeful and willing to give online dating another shot, but in a different way. These are the individuals who often find success and become the ones who inspire others.

Willingness to Explore and Try New Strategies

The common thread among them is that they have recognized that their previous approach to online dating hasn’t yielded the desired results, and they are seeking feedback and guidance to improve.

Taking Responsibility Is Crucial

I teach my clients the importance of regular communication with me – I have equipped them with tools and even assigned them homework! (Yes, it requires dedicating 30 minutes, three times a week, solely focused on achieving positive outcomes online.)

Being accountable brings about positive results. You have made the decision to find “the one”; you are no longer just discussing it, but actively taking the necessary steps to meet the right person.

So, Is It Possible to Meet Someone Through Online Dating?

I believe the chances are quite high if you approach it correctly, with a positive mindset, a well-thought-out strategy, and a genuine openness to welcome someone new into your life.

Let’s Have a Conversation:

What is your online dating strategy? Do you have one? On a scale of 1-10, how would you rate your photos? Are the messages you send men quirky, unique and a tiny but flirty? Do you always close with an interesting question? What are the typical messages you send? I’d love to see an example and give feedback!

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