College was not my shining moment. Some girls thrive in high school, others blossom when they go off to college, I am convinced that I will have my shining moment when I finally come into my own and no longer be the clumsy, awkward, ball-cap-wearing, no-makeup five days a week, pizza-and-brownie-binge-eating girl that I currently am and love. Maybe in my 50s?

Probably not

But being a late bloomer to life really meant for my dating life that neither my highschool or college years were filled with fun, romantic dating experiences. In fact, I’d characterize most of my dating experiences in college as awkward. And my high school dating experiences? Non-existent.

I mean when you go to a conservative college where people call dating “talking” can it actually avoid being awkward?

Ironically, or maybe I’m just a glutton for punishment, that awkwardness is part of what made me decide to start dating. I mean, being a homeschooler most of my life offered me many advantages, social skills not being one of them….

The first date I went on to end my 4 year hiatus (not that I was dating much before that), was with a guy I met online who was significantly older than me.

Now age really is just a number. Unless your 16 (the biggest accidental “date” mistake ever)…

But more influential than age is place in life, values, and to reference previous stories ability to get oneself to a date, no missing teeth, and having non T-rex reminiscent baby hands. Picture it I dare you.

I have gone on dates with, or had interest in, guys who were younger, older, or my age so it wasn’t a big deal to me to go on a date with a guy who was 12 years my senior. It was more of a big deal to me to go on a date. Now that I have a few dates under my belt I have to do less self pep talks to psych myself up to go out. But this first one took alot of psyching up and pep talks from friends and my “get psyched” playlist (which mostly consists of rap music from the late 90s and early 2000s). I remember thinking about just how awkward I can get, especially when it comes to guys that I like.

Now I had worked with 30 men for a year and knew that I am totally capable of conversation and being a normal human…But apparently something about the loaded nature of dating makes my brain and words turn to mush and the content of my thoughts/words to be things like:

Soooo…. do you like cheese?

Showing up to the restaurant to meet up with Ben was really an experiment. The number of times I had to remind myself in the car on the way over to “BE A NORMAL HUMAN BEING DESIREE” is probably an embarrassing amount. But I walked in, saw him sitting at one of the high top tables, took a deep breath, plastered a fake smile on and introduced myself. Thinking the entire time

Why do I feel like he looks like one of my friends’ dads??

Turns out I was Ben’s first date too. Since his divorce. And really? It might have been a littleeee too early for him seeing as we spent at least 60% of the night talking about his divorce and his ex-wife and the pain that came with all that.

In case you are wondering what made up the other 40% of the date
– 20% “I should totally buy a bar!!”
– 10% talking about his two precious kids- one of whom was only 9 years younger than me…
– 5% talking about our future together- Seriously? why is this a thing on first dates
– 45% total and complete awkward silence. Just staring. At me.

I remember after the date Ben texting me and telling me how refreshing it was to be able to sit across the table from someone and be so comfortable around them that there was no need for conversation

Clearly he had been married for a long time…

Now this date was long before yours truly became Rev. Des, so I have to admit that probably the best part of the date was the glass of wine I had to sip on when those awkward silent stare moments came. Probably can credit at least part of my courage to face the awkward to that.

Racing through my mind is everything I had googled before the date about questions to ask on a first date and every little tip for small talk I had ever heard in my life. Thankfully “Do you like cheese?” is not what I said and I fumbled through the date as best I could acting mostly like the adult human I was aspiring to be.

On this date I feel like I was part therapist, part cheerleader, part storyteller and definitely part muse (seriously dude, stop staring its weird). Now I don’t have any issue with dating someone with kids. I love kids and plan on fostering, adopting, and having a house full of children till the day I die (is 27 children too many??). So being a single dad is certainly not a deal breaker in and of itself. However, when your kids are almost the same age as me, I just feel like we are probably going to be in a very different place in life.

After dinner Ben walked me to my car and said all the nice things that you say to a person after a date. Looked like he probably would have tried to kiss me if not for the giant cold sore on his lip so instead he went in for a hug.

I got in my car and breathed for maybe the first time all night. Now the date wasn’t bad. He wasn’t a terrible guy. Breathing my sigh of relief had more to do with realizing

“Wow. I can totally do this!”

Honestly, I think that if it weren’t for the things I learned about myself and the ways I grew from those awkward moments and dates, I wouldn’t have the same confidence to approach dates as I do today. I still have awkward moments where I say all the wrong things and pre-date moments where I am googling things to say. But I’ve realized that I can survive and learn from all those awkward moments.

And all the leftover awkwardness just is part of my clumsy, awkward, ball-cap-wearing, no-makeup five days a week, pizza-and-brownie-binge-eating self that I currently am and love.

Tips for surviving awkward conversations:
1. Relax.
2. Be curious. Now you don’t have to be nosy, but curiosity helps you to ask your date questions about themselves. Don’t get too in your head about what questions you are asking. Just be interested in getting to know them and their story.
3. Think of a couple funny stories or experiences ahead of the date to tell if you run into a real lull in conversation
4. Take the opportunity to get to know yourself. Don’t know how to answer the “what do you do for fun” or “what kinda stuff do you like to do” questions without feeling cliche? Well, take some time to learn about what you enjoy! Try some new things! Be adventurous and KEEP trying new things. Not all of them will be liked but you will discover new things about yourself.
5. Relax. It’s not the end of the world. Or the beginning of it for that matter. It’s just a conversation. Have some fun. Be confident and embrace who you are.

What’s the most awkward thing you’ve said on a date?