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The Introvert’s Guide to Dating

November 22, 2016
You don’t have to let her win. You DO, however, have to make sure nothing is stuck in your teeth. (image via wikimedia)

He doesn’t have to let her win at the board game. He DOES, however, have to make sure nothing is stuck in his teeth. (image via wikimedia)

Dating can be tough for anybody, but it was especially rough for an introvert like me.   I’ve never liked talking to people I don’t know very well.  I’ve never liked unpredictable situations.   To make matters worse, people who weren’t familiar with me have always thought I was kind of awkward.  Despite these disadvantages, I eventually I learned to thrive in the harsh world of dating.

25 years ago when I was dating, it was easy for me to tell if I was a good dater or not.  From what I had heard, a good date usually ended a certain way, and none of my dates were ending the way I had heard they should.  I knew I was getting better at dating when more of the dates started ending right.

Soon after that, I ended up with a girlfriend, and then I got another one (not at the same time), and later on I even got a fiance who became my wife.  My dating had become so successful that I had to quit dating.  If I’m lucky, I won’t ever have to date again.

Looking back, there were a few things that an introvert like me had to do to make each social outing a cringe-free experience, so here are a few lessons that I learned.

 Be the BEST version of yourself.

“Be yourself” by itself is lousy advice.  During my dating years, being myself meant reading comic books and watching football games while wearing a superhero t-shirt and baggy shorts.  Today, wearing a superhero t-shirt is socially acceptable, but it wasn’t 25 years ago.  That was a bad version of myself to use as a first impression.

The story about how I figured all this out is kind of long (60 episodes, starting here), but I eventually learned (or was taught).  Wear nice clothes.  Clean the car.  Be ready to pay for anything, and don’t complain about the price.  I wasn’t the most handsome, most fashionable guy around, but I was acceptable to the kind of woman I was dating (I had surprisingly high standards).  That by itself meant I was doing a lot better than I had been.

Stay away from unpredictable food.

Too many things can go wrong when you’re eating food on a first date.  You can spill something on an inconvenient location.  You can get food stuck in your teeth and not know about it.  Hot food can cause your nose to get runny.  Bad food might cause stomach problems which lead to embarrassing public situations.

You can’t avoid food on most first dates, but you can be careful about the food you choose.  I learned to go for thin sandwiches and fries, and I let them cool a few minutes before I eating.  Thin sandwiches don’t spill.  Fries are manageable also and don’t cause a runny nose after they’ve cooled down.  Once I found my “safe food,” I never had another food disaster on a date.

Script it out.

Sometimes my mind blanks out when I’m in unfamiliar surroundings or situations.  I’m not scared or anything.  I’m just processing, but to others, it looks like I’m freezing up.  Sometimes when I’m processing, my conversation skills deteriorate, and that can make a lousy first impression, so I learned to script a few conversation starters.

When on a date, I stayed away from the topics of weather (unless it affected the date), politics (unless I decided I wanted the date to end early), and sports (unless my date showed up wearing a jersey).  I usually had snappy patter prepared about music, entertainment news, and puppies.  I also pretended to like whatever music my date enjoyed, unless it was too sappy (in which case my date was probably testing my masculinity).

Learn to dance.

Dancing is a great skill/activity for an introvert because we don’t have to talk.

Just to be clear, I never succeeded at dancing.  When it came to dancing, I was a failure.  I think today I would be called a dancing fail.  An introvert friend of mine, however, became very good at dancing and met his first (and second) wife dancing in a certain style.  He became very good at dating, but not so good at marriage.

Me?  I couldn’t dance without injuring myself and others, so I got better at other activities like bowling, pool, and putt putt golf.  Women love beating guys at putt putt golf.  I’m not saying a guy always has to let the woman win.  In my case, I was always doing well just by keeping the games close (I’m horrible at pool, bowling, and putt putt golf), but my dating game improved drastically and led to other activities (like sunset walks and European vacations).

The point is that quiet, non-aggressive guys can find ways to succeed at dating without coming across as trying too hard.  Follow these rules (I’m sure there are more and better rules, but this is a blog and it’s free so what do you expect?) and you can be an introvert success story too!


It has been over 20 years since I’ve had to worry about dating, so maybe some stuff has changed since then.  What advice do you have for introverts who are dating today?  Since my advice has been male-oriented, what advice is out there for the female introvert too?


And while you’re thinking about that, here’s the perfect book to read before, during, or after a date.

From → Pop culture

  1. the reality of dating, last time I did it anyway, was to find a person who’s bs didn’t bother you and who accepted your bs. so be you, so that you get the person who isn’t bother by your lack of dancing skills. LOL

  2. dating is a complicated endeavor that introverts should learn the skill of being sincere and genuine…. yet at the same time an exciting and no-frills individual….

  3. dating, I think, is difficult for everybody. I am an extrovert by any means, I find it very easy to talk to complete strangers. but on a first date – an earnest one, where one is actually emotionally involved – I was as nervous as can be. It’s been a long time ago, but still, it is not something enjoyable to recall. All tense, all nerve wracking…

  4. Fantastic advice for the introvert – every point sound, especially those about food choice (never spaghetti – never an extra hot curry that might you look too macho and result in tears) and being the best you can be. No one wants to see the real us on a first date – they expect to see the polished up, Sunday best version, not the slobbing around in your pyjamas, eating a whole tub of Ben and Jerry’s us.
    One thing I’d add to the list for introverts of both sexes – be cautious of alcohol. One drink is tempting, to loosen you up, shed the tongue-tied nervousness. But drinking a whole bottle of red wine to yourself then dancing the merengue barefoot on the table, bread stick clenched between your teeth will guarantee you get the cab home alone.

    • Yes, I’ve seen many a person screw themselves with drinking too much. I would also add that it was good on the other person for knowing right away that they’d be getting into a bit of craziness with that one! For me, the breadsticks would be my downfall. 🙂

  5. I think I will let my introvert 23 year old son read this. Good advice.

  6. dating is tough for writers… nobody wants to hear you talk about the thing that interests you most, your latest project. Tough as dating is, marriage is harder!

    • You’d think more people would be interested in the writing process, right? The length of time it took me to develop that character or rewrite that paragraph is worth something!

  7. mcneilljared permalink

    Good stuff. Seriously. I’m an introvert myself, and it wasn’t until I reached 30 that I met my wife. I was beginning to wonder if it would ever happen, but then I had this conversation and everything changed. You just never know.

  8. What awesome advice! I never like to meet new people, in any situation, without having a cadre of ‘conversation starters’ to fill the silence. If you’re truly desperate for conversation you can use this Hail Mary- If you were an M&M what color would you be and would you eat yourself?
    Please only use as a last resort!

  9. Wow, I really liked your point of view on dating as an introvert. I am an extrovert but have been interested in guys who are introverts and it can be weird waters for me. I enjoy the incite on how you prepare and feel this would be a good read for some of my introvert friends in grad school hahaha. Feel free to check out my dating page 🙂 ciao

  10. This is such great advice you’ve piled in here. I’m the introvert in my group of friends, so when we go out it tends to take guys a bit more time to notice me in the group conversation, but once a guy does take interest, I feel I can hold his attention pretty well. So I would say that a bit of patience is good to have. We may not grab the attention right away, but if we cultivate our own minds, talents, etc. as you’ve mentioned, we’ll help people want to stick around.

Trackbacks & Pingbacks

  1. The Introvert’s Guide to Dating — Dysfunctional Literacy – anewme
  2. A Dating Guide For Introverts – I w a n n a b e a l a d y

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