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Biggest Online Dating Mistakes: 11-Years of Bumbling Hits and Misses

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I write a lot about online dating. I have enjoyed three successful online-started relationships. This includes my current girlfriend, who crossed my path on After all this time as a single dad dating, 11-years since my divorce, I’ve learned a number of fundamental lessons on how to not waste time and not miss golden tickets to love.

Defining “Online Dating”

Well, sure, it starts online, but unless you are looking for a sexting, Zooming, FTing partner, you’re going to have to go from ONLINE to OFFLINE. Let’s just call it eDating. No, that sucks. Let’s just call it dating.

The Big Dating Machine

  1. Bumble
  2. Tinder
  3. Match
  4. Hinge
  5. eHarmony
  6. OK Cupid
  7. Facebook Dating (mobile only)

If you’ve spent any time on any of these apps/sites you are familiar with the process. For those of us who re-entered the dating pool after many years of being married, there is a bit of a learning curve. I’m going to give you a few big OOPS moments so you can avoid my mistakes.

My First Online Dating Mistake: Trying Too Hard

Trying to hard to be cute, available, and eager. The first near-miss in my online dating history occurred 30-minutes after a very successful “hello date.” At the end of our meet and greet I walked her back to her car. She said, “I’d be okay with you calling me, if you want to get together again. I think we should hang out.”

BINGO. That’s a home run for the online-2-offline progress. I was elated. We’d also shared two margaritas each over the course of an hour. I was buzzed. As she drove off I began writing love poems in my imagination. (That’s what I do, I ‘get off’ on romance.) About 20-minutes later, when I got home, the poem in my head was done and I decided to text her at the phone number she gave me. After my two texts:

  1. expressing my agreement at our connection
  2. suggesting the next opportunity

I waited. The chat bubbles appeared and stopped. Appeared again and stopped. About 10-minutes after my texts, she texted back, “You need to slow your roll.” The text conversation went downhill from there. I never saw her again.

My Second Online Dating Mistake: Going for Or Accepting In-Person Meetings Too Soon

Men get 1/10 the connection requests that women get online. Women are flooded with invites and offers. Men are starving for a single REAL connection. But the process is the same for both men and women who are looking for a real partner and not a fling.

The 11 Essentials on an Online Dating Strategy

  1. Read the profile
  2. Look at all of the pictures. (See if you can spot the ONE that is real or the ONE that gives you exciting vibes.)
  3. Exchange several casual and witty DMs
  4. Let the woman go for the ask (phone number – to text, date and time for an inperson)
  5. Always, Always, Always Talk On the Phone
  6. Ask where they would like to meet
  7. Be on time
  8. Be honest, no lies, no ghosting, no catfishing
  9. Wrap early and have a time-bound activity about why you can’t stay longer
  10. Tell each other YES by asking for a next date
  11. If either person has to ask, “So….?” the date was a miss. Move on.

My Third Online Dating Mistake: Meeting for Drinks

If you are a drinker, and drinking is a big part of your joy, maybe bar dating is fine. I’m the opposite. I don’t go to bars, happy hours, for fun. I don’t drink much. So, the idea of meeting for a glass of wine, then paying for it, when I’m not that into it in the first place, well, why would I meet you at a bar? I’ll suggest Starbucks or going for a walk around the local lake instead.

As you drink with a potential date, and you’re getting revved up, the alcohol is going to amplify the HIT. The alcohol will also dull your ability to sense the subtle red flags that are going up all over the place. First dates are meant to inform both people if they want a real date. First dates are the last step necessary to launch a relationship. If it goes well, if the lights are green on your navigation dashboard, you want to be sharp. Being buzzed is a great way to fall into a bad relationship. If the sexual chemistry is on and your getting buzzed, well, that just multiples the high. Do you want a “high” relationship? I think not.

“Let’s meet at the tennis courts.” And my perfect match says, “Oh, great. I haven’t played in a while, but I’d love to.”

My Fourth Online Dating Mistake: Sex and Drugs and Rock ‘n Roll

My fourth attempt at an LTR was quite different than anything I’d experienced. We went through many of the pre-in-person steps. And we’d had TWO absolutely electrifying phone calls. And we made plans to meet for breakfast. The chemistry was on fire within 5 minutes of starting our phone call. She was aggressive and funny. She was also unafraid to bring up sex. Our in-person date was a bonfire of a success. We kissed in the parking lot for 10-minutes before she drove off.

So far, this was not a mistake. But, I had been blinded by her sexual intelligence and had no knowledge of her emotional intelligence. Sure, we talked a lot about Brené Brown in our first phone call, but she was more of an enthusiast of BRAVING, not much experience with actually holding an emotional center. And that was the big fail. Things blew both of our normal lives into a blazing frenzy. She lived in a nearby town.

“So, I’m not sure how this is going to go,” I said in one of my early DMs, once we’d established mutual intentions. “Well, I guess we’d spend nights at your place of my place depending on what we were doing.”

Wait, wasn’t that skipping a step or two? How do you “date” someone who lives an hour away? How do you stay at the potential date’s house after the date? Yeah, we were ON but we were on a trajectory straight into bed. And, as it turns out, it was the sexual ride of my life. Relationship potential (20-1 odds) was a long shot. But who the fk cares. When the bed is burning you don’t ask questions you go for more fuel.

In the end, it wasn’t a failure so much as an ecstatic dream sequence that took about 7 months out of my progress. She was lovely. She was doing the best she could. We parted as friends. “When I love someone,” she said. “I always love them.” I hear she’s getting married to a small-town man a few villages away. Good for her.

My Fifth Online Dating Mistake: Casual Sex

The only casual sex I had was the WIN I experienced on a first date from Tinder. We met at a restaurant and proceeded to down a couple of margaritas the sexual fires lit up between us. There was so much YES and DO ME in the air we decided to skip the second margarita. There was a split second where she nearly suggested I just follow her back to her place, but the moment came and went. I hugged her at her car as she drove off. I was buzzing.

About 15 minutes later I texted her. “I’m not done with our conversation. When can we see each other again?” Her response was immediate. “Now, if you like…”

The experience was odd. It was not entirely unpleasant. BUT, it was not what I was looking for. And this woman, was not at all what I was looking for. The hallmark of this second date was how proud she was of the “boobs my ex-husband bought me after the divorce.” Ouch! “Um, before your divorce, you mean?” “No, the alimony.” She even let me know they had cost $5,000 per boob. “Aren’t they perfect?” “Yes, absolutely.” And that was the woman with perfect boobs. We did not initiate a third date.

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Coming in some future installment:

  • My Sixth Online Dating Mistake: Too Many Connections, Too Little Vibe
  • My Seventh Online Dating Mistake: Reaching Above Your HOT Class
  • My Eighth Online Dating Mistake: Too Much Flexibility and Understanding When Trauma Appears
  • My Ninth Online Dating Mistake: Getting Back Together with a Failed Partner
  • My Tenth Online Dating Mistake: Not Having Your Focus on an LTR
  • My Eleventh Online Dating Mistake: Pursuing Unavailable Partners
  • My Last Online Dating Mistake: Thinking Sex is Just Sex

Wrapping Up the Online Dating Process

Write your profile honestly. State what you want. State what you’re bringing to the party. Then edit, ask, talk, phone, and get to know them before you go for that intoxicating “first date.” And, in my opinion, avoid meeting for alcoholic drinks.

“Let’s go for a walk, it’s a beautiful day,” is the perfect opening.

“Sure, what time?” Is the perfect response.

From there, you’ve got to have your plan in place so you know how to evaluate potential partners for the long-term relationship you deserve.


John McElhenney
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