12 Online Dating Mistakes To Make Your Valentine’s Day Extra Special (not!)

Talking to daters all day, every day for what feels like 30 years (but who’s counting?), I’ve heard it ALL. The drama, the heartbreak, the ghosting sagas, and, of course, the desperate cries of “WHY IS THIS SO HARD?!”

Everyone is thinking about Valentine’s Day – love it or hate it, you know the media and every retail outlet is reminding you of it. Boxes of heart-shaped chocolates assault as you walk in CVS to red Valentine bears holding expensive fragrances at Neiman Marcus. You just can’t escape.

But your attitude can… or can’t it?

So, is this you, the complainer about dating and Valentine’s Day? Time to get a (love) life!

1. Online Dating Is Exhausting

Are you running a dating app or using one? If it feels like a full-time job, you’re either overdoing it or just thinking about it too hard. Pro tip: If you’re spending more than 90 minutes a week swiping, you might as well add “Dating App Overlord” to your LinkedIn profile.

2. I Don’t Even Know Where to Begin – It’s Overwhelming!

You just got out of a 10-, 20-, or 30-year relationship, and now you find out there are 1,400 dating apps?! I’d be overwhelmed just typing that number. Do we really need an app just for people who love sourdough bread? (Yes, that exists.) No wonder you want to quit before you even start!

3. I’m So Discouraged

Because you went online for two weeks and didn’t meet The One? Honey, Amazon Prime has ruined your patience. Good things take time. Give it three months, and I almost guarantee you’ll have a different story.

4. All the Good Men Are Married

Oh, look – another entry in the “Urban Myths of Dating”! Funny enough, over 50% of my clients are men, and they swear all the good women are taken. So, unless there’s a secret underground society of “good people” hiding from us all, I’m calling BS.

5. No One Responds to Me!
Okay, I’m gonna be blunt: YOU are doing something wrong. If your opening line is “Hey” or worse, a wink emoji, you deserve to be ignored. Try something fun, weird, or specific. Trust me, it works.

6. I Send SO Many Messages and Get Zero Responses

Do you, though? I bet if you kept a message log (oh hey, there’s one on page 401 of my book 2nd Acts: Winning Strategies for Dating Over 50), you’d be shocked at how little you’re actually engaging. Time to bust that excuse!

7. It’s a Full-Time Job, and Why Can’t I Meet Someone Organically?

Because organic is for blueberries, not dating. If you’re waiting to meet someone in a coffee shop like it’s a rom-com, you might as well start carrying a boombox and wearing a trench coat in the rain. Times have changed!

8. The Quality of People Online Is Terrible

This isn’t 2005. Things have changed. I have three clients a week meeting long-term partners online. And for the record, I met my guy on my sixth first date. (Even my ex-husband met his now-wife on Bumble. No, I’m not bitter. Much.)

9. The Dating Sites Are Awful

Yes, some of them are dumpster fires. But others? Want to know which ones? Read pages 97-113 of my book, where I break it all down. And no, just because your brother found his wife on FarmersOnly doesn’t mean it’ll work for you. Unless, of course, you own a tractor.

10. I’m Nervous People Will See Me Online and Think I’m a Loser

Newsflash: It’s 2025. You’re already on LinkedIn, Instagram, and Facebook. One of my clients – a famous athlete – was worried about this until I reminded him two of his teammates met their wives online. He got over it. You will too.

11. I Was Married for 30 Years, and the Idea of Dating Again Terrifies Me

OF COURSE it does. You didn’t walk down the aisle thinking, “Can’t wait to do this all over again someday.” But new things are always scary. Get some help, build your confidence, and remember: 45 or 64 is not old. You have plenty of time for a second great love. Maybe call a dating coach.

12. Online Dating Won’t Work for Me

Why? Are you a vampire? Do you live on a deserted island with no Wi-Fi? Because unless you’re actively sabotaging yourself, it can work for you. Let’s talk about why you think it won’t – because that’s some 1990s energy we need to leave behind.

There is no one-size-fits-all for love.

Now, do people ever call me and say, “Andrea, I’m SO excited to try online dating!”?

LOL. No.

But guess what? If you take a chance, you might just be calling me in a few weeks with a totally different story.

Start with my book (hot off the press last week!) to get in the right mindset. It’s got 14 worksheets, 14 QR codes with videos from me, and a roadmap to help you stop swiping in frustration.

And if you’re really ready? Call me. Let’s make this fun!

Also read, The Top 5 Dating Trends in 2025 – and What’s Totally Out.

Let’s Have a Conversation:

How do you celebrate Valentine’s Day? What’s the best Valentine’s Day you ever had? Share those stories!