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My First Online Date Ever

I might have it all figured out now… but it came at a price! I’m excited to share with you my first online date ever!
When I first started dating with a purpose, I had no idea the uphill climb in front of me. I was lost, confused, frustrated, and unsure just like so many other women. This is why I get so much joy out of showing women how to expedite the process and learn from my experiences!

Despite the fact that it was filled with ups and downs, I still believe you should try online dating. I’ve made many mistakes (that you can learn from!) and have the stories to prove it! Let’s take a look in the past…

Hello World of Online Dating

It was after the divorce and the 3 month “rebound relationship” had ended. I decided I was ready to meet someone great, so I made the brave decision to enter into The World of Online Dating.

sky-space-dark-galaxy-medium*Cue the Twilight Zone music please

I got started on creating a profile. I wrote my “about me” section, posted a few photos, and made the profile “live”. It was official: I was an “online dater”.

Pretty quickly, the “messages” (not to be confused with an actual message- because an actual message requires thought and substance) began to fill my inbox.

∗Allow me to interrupt this broadcast to deliver a Public Service Announcement to any and all men that stumble upon this post:

“Hi” / “Hey” / “What’s up” / “Hi Beautiful” / “You’re cute” / “Your cute” / etc. are NOT messages! Messages are meant to start a conversation… so please: start one. Thank you. We may resume as scheduled.—


As I read said “messages,” I couldn’t help but wonder, “Is this really the type of man I attract??”

I honestly wasn’t interested in any of the men that wrote me the first week. As a strong and independent woman, I decided to reach out to a few men myself. I sent messages to several men and waited for their response. What response did I get? Crickets. (That’s a topic for another time!)

Really? NONE of the men I’m interested in will write me back?

That’s when I realized this “online dating thing” wasn’t going to be as easy as I thought. Two weeks later (and probably 100 “messages” later) I finally got a “message” from a guy I at least thought was attractive:

Finally! Someone Cute!


Jason (I didn’t know his name yet… but I would soon) was 37 years old and had a graduate degree. He looked attractive in his (20!) photos… so much so that I chose to over look the number of car selfies. His profile actually contained some detailed information:

1st OLD Ever Profile


I noticed the typos too… but I tried to remain optimistic. (Don’t judge me! This was the first message from a cute guy that actually had details in his profile.)

Sure, there were a “few” grammatical errors and spelling mistakes… but does that stuff really matter anyway? (Ok, now I’m judging myself. That’s a TON of typos!!! What was I thinking?!)


I wrote him back a brief little response:

M2Oh my goodness, I’m so clever!

He wrote back:


Ok ok… let’s play it cool with the response. I wrote:


His next message:


Huh? Ummmm yeah. I got the name before. That’s basically all you said in the last message. What do I say now?


Naturally I responded:


Riveting interaction, right? Well, if I haven’t put you to sleep yet I could with our texting.


Jason wrote me the next day and said:


Oh. So Singles Text A Lot These Days

It was news to me that we were even having a conversation. Still, after work I decided to send the first text:

Jason Text1

Aaaaaaaaaand….. we were off! Off to texting about his decor, his sister’s (Shana!) wedding, his parents’ house in Colorado, where he was driving to for work, when he got off the phone with his Dad, what movie he was watching, when he had a belly ache, what he was shopping for, (I could keep going… but I think you get the point!).

Then the photos started rolling in. The first photo he sent me was of dinner he was making: Tacos.

Yep. This is the actual "Taco" photo.

Do I really need to see photos of the food you’re cooking?

But what did I know? I was new at this whole modern dating thing.

Car Selfie... with his Mom.

Car Selfie… with his Mom.

Pretty quickly, the texting and photo monster got out of control.

I was receiving photos of him in his car, out with friends, with his Mom, how much he was spending on gas, what song he was listening to, past photos of the family vacation, his sister, of the sunset he was watching, (once again… I could keep going!).

He sent me 32 photos in the 3 weeks that we texted.





I engaged in the photo game just a little bit. I did show him my living room after he showed me his:


I also sent one photo of me out with a friend. I really didn’t get any reaction from my photos and it felt pretty awkward… so I ended up sending only 2 photos to a stranger (and that’s probably 2 too many!).

Somewhere in the midst of the multiple “Good morning,” “Goodnight,” and “Here’s what I had for dinner” texts… we set up a time and place to meet.

He suggested dinner at a pretty casual restaurant (similar to a Chills).

My First Online Date Ever

It’s Official. My First Time is Happening

Now, remember: this was my first date from online dating… EVER.

I was extremely nervous getting ready that night. Of course, I had a new pimple (hormonal- the worst kind!) that I massively stressed over covering. I had no idea what to wear and tore through my closet trying on everything I owned. (More on What to Wear on a First Date.)

I settled on a cute girlie shirt, skinny jeans, and sandals.

I’ve always been a pretty outgoing person… but I was so nervous I was shaking on the drive over. I’ve been talking to (correction: texting!) this guy for weeks! I already “know” him… this should be fun… right?

I texted him as I pulled into the parking lot. He was already inside waiting. I walked in and instantly knew who he was. I (think?) I smiled at him and gave a little half hug.

Hi, Nice To Meet You?

When meeting someone from online, the first thing you want to do is get a good look and see if they actually resemble their photos. This is just human nature. It’s hard to actually get a closer look until you’re settled and sitting down.

He looked similar to his photos… but something was off. His voice was nothing like I imagined this 6’2 man’s voice to be. There was a slight lisp… but nothing too severe. I was still mildly optimistic.

That didn’t last very long.

I’d Like Extra

pexels-photo-70497-mediumWe said our hello’s and proceeded to look at the menu so we could place our order. When our waitress greeted us he became overly conversational with her. He wasn’t flirting at all… just very chatty with her. He was quick to share details about his day and offer his opinion of different food items.

She offered a meal suggestion and he let her know he didn’t need one. Kinda awkward.

She returned with our drinks and asked for our order. I ordered first… then he did. This was how his order went:

Him: “I’d like the hamburger… with extra. Then I’d like the fries… with extra.”

Waitress: “Ok, great. Hamburger and fries. What did you want extra of?”

Him: “I’d like both with extra.”

Waitress: “Extra what?”

Him: “You know, just extra.”

Waitress: “Ok… I just need to know what item you’d like extra of…”


Me: My eyes were bouncing back and forth like I was watching Wimbledon.

Him: “Just extra of something. I want the extra on both the hamburger and the fries.”

Waitress: “Alright. So do you want extra cheese? Sauce? Bacon? What exactly?”

Him: “I like surprises. That’s why I say extra for the hamburger and the fries. You pick what the extra is.”


W. T. F?!

I smiled at the waitress as she took my menu and walked away.

“It’s not that hard,” he proceeded to tell me. “I order things with extra all the time. It’s fun because you really never know what you’ll get.”


Jason’s life philosophy #1:  It’s fun to order extra. 

We made light conversation about the food at the restaurant. I asked him a few questions and he gave (very long winded) answers. I’m all about collecting information about people on first dates but in order to connect you both need to be disclosing information. I started to realize that he had zero interest in asking me anything.

I decided to stop leading the conversation and just see what he did. This is what happened:


I made a comment about something in the restaurant and then stopped talking. Once again:


images(Ok, I can’t help myself. This is making me think about the comedian Jeff Dunham’s puppet that says, “Silence! … I keel you!” I would have much rather been having dinner with Achmed at this point.)

I rode out that silence wondering what would happen next. That’s when he let me know another nugget of information about him.

Him: “Oh, something you should know about me is— I don’t believe in asking questions.”

Me: “Huh?”

Him: “I don’t believe in asking questions.”

Me: “What does that even mean?”

Him: “I just don’t believe in asking questions at all. The conversation will flow as it should.”

Me: “So how do you get to know someone then?”

Him: “I just don’t believe in forcing anything. The conversation should flow organically.”


Jason’s life philosophy #2:  Don’t ask questions. The conversation should flow organically. 

So how does a conversation “flow organically” you might ask?

Easy: I ask a question… he answers. I ask another question… he answers. I ask yet another question… he answers… and then I randomly decide to answer it myself just so I can hear my own voice for a moment instead of his.

Shauna’s life philosophy #1: I’d rather be eating Ramen with my cats than eating a burger with Jason ever again.

The date ended civilly. I thanked him for dinner and gave him a brief hug on the way out. We texted 9 more times after the date. It should have only been 2 (one from him and one from me letting him know we weren’t a match) but in those days I was guilty of occasionally committing the crime called “the slow fade”.

The Important Stuff

They say you never forget the details of your first time. Someone had to take my “online to real life” experience, and Jason was it. Here are a few additional facts in case you were wondering:

  • His nickname among my friends became “Extra Jason”
  • The waitress gave him extra bacon on his hamburger and extra cheese on his fries.


Good news ladies! It would appear that “Extra Jason” is still available!


Jason3After I found our original emails to each other, I clicked on his profile link. (Yep… you read that right. I still have every last email and text! That’s why I can share so many exact details with you!)

Low and behold —almost 5 years later— “Extra Jason’s” profile is still up and active. The pictures are exactly the same and so are the grammatical errors. Maybe you’ll have “extra” luck allowing the conversation to “flow organically” than I did.



(P.S. Don’t give up on online dating. Many ups and downs later, it’s how I met Kevin!)

2 Responses

  1. Leslie says:

    HAHA! This is too funny! My favorite post thus far. Great job!

  2. Stacy says:

    OMG this sounds like so many of my bad dates! I can’t believe he still has the same profile active!!!

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