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Dating Tips For Shy People

Updated on May 21, 2013
Awkwardly Shy
Awkwardly Shy

Dating and the Truth

If you've seen the movie "The 40 Year Old Virgin" then you know hooking up can be quite challenging if you've never done it before. Let’s be honest, drumming up enough confidence to ask somebody out on a date is like conquering Mount Everest if you’re shy by nature. Though being shy is not a character flaw it definitely puts you at a disadvantage in the dating scene since succeeding at winning private time with a person of interest is a game of chance that requires you to have a short memory of defeat and enough confidence to keep on fighting. When you’re shy it takes that much more effort to go back out to the playing field after failure because tendency is to be introverted and the idea of sharing your whole life story with someone yet again is stressful considering success is not guaranteed. Well you should not feel that way. Here are some facts, according to me, and tips that you can use as a primer for success so that the next time you take your balls, or lady parts, in your hand and step off the cliff you will feel less like deer in the headlights and more like a confident buck about dating.


  • People either want to date you at the onset of a meeting or they don’t and this depends mostly on looks. If you are cute you have the world by the balls. If you are anything but cute you need to rely on other factors to have success. Don’t be mad, it’s the truth. All ladies will agree Brad Pitt is hot. All men will agree Giselle is gorgeous. For everyone else like me, wee have to work a bit harder to get bites using the gifts god gave us. What if you are not hot? The easiest solution is to look like an ex-boyfriend or girlfriend or resemble a dad or a mom of the person you are enamored with. For some reason love burns images in people’s brains and if you can fit that mold, you’re money baby. She only dates bad boys? Become a bad boy. Etc., etc.
  • Wake up and realize the odds are stacked against you. There are 6 billion people on this earth. A good portion of this number of the world’s population are either old people, kids, married, in jail, or just plain out of the pool you want to be in. The rest of the contestants in the game are all doing the same thing you are doing meaning there is some serious competition to deal with. Once you are cool with playing the victim/hero “me against the world” role with you can have fun with this concept even as a shy person. Try new things. Find a niche. Learn from mistakes. Remember, “You win some, you lose some, but you live to fight another day” courtesy of Pops from the movie Friday.

Chill Spot
Chill Spot

Go To Places You Like: That same anxiety people get from public speaking can handcuff your personality if you're in an environment that makes you feel uncomfortable. Why go to a nightclub if you don't enjoy dancing? Why go to a pub if you're not a drinker? By hanging out at places that appeal to your tastes you feel more at ease with yourself making it easier to strike up a conversation as a shy person. What a concept!

Find Your Avenue: Let’s say you have tried all of your favorite hangout spots to seek attention and no one was paying any attention to you. It’s time to go to plan B, covert operations. I have a friend that meets girls at salsa clubs. He took lessons, learned to dance with a partner, and now meets women in every new town he travels to for work. As a shy person dancing is a great avenue to explore since it is pretty much understood that if you are a guy you will take the lead and if you are a lady you will be asked to dance. If you are gay or lesbian person then I’m sure some combo of those two roles will occur if you are simply in attendance. You don’t have to really converse since the music is so loud you can only move to the beat and the bonus is you get to rub all over each other in rhythmic bliss. Win win! If you enjoy each other’s company then you can start the chitty chat.

Selfless Acts Welcomed
Selfless Acts Welcomed

Be Selfless: Self-preservation tells us to think of ourselves before we think of others. Unfortunately, this natural instinct sometimes goes beyond the acquisition of basic needs, in this case basic conversation, and becomes a fatal flaw to many of our goals. Don't press your opinions or ideals on other people if you are shy since your words will naturally be limited. Instead focus on the simple victory of attaining a conversation and let the other person shine, unless you're a closet pimp or preacher and harbor helpless victims seeking love any which way they can get it in which case good luck to you and your gospel. People love a good listener especially if you can hold a conversation longer than a discussion on today's weather forecast.

Hold A Conversation: Like the previous piece of advice it's crucial to be a good listener. It's equally important to be interesting via what you say about yourself. A combination of these two key conversational elements can turn you into a Casanova overnight. Now you don't have to be the funniest person nor the coolest person, but you should definitely be able to relate to what your date is saying while expanding on the tone with your own experiences. Think tennis. One person serves while the other returns and it goes back and forth until somebody scores. So score already!

Use Props: Most stand-up comics frown on other comedians using props because it gives a certain advantage. I guess it's like cheating on a test by having a sheet of notes tucked into your sleeve. I say props are good for dating because they add an additional element to the conversation. "What kind of props are you talking about?" you're asking. Like a mechanical bull. Let's say you're at a country bar or restaurant having lunch with somebody. There's a mechanical bull in the corner staring at you. Why not jump aboard and give it a shot for laughs if the conversation has been sparse so far? You may look like a complete idiot or you may turn out to be more like John Travolta in "Urban Cowboy", either way you'll have something to talk about for the next 20 minutes and as a shy person that is pure gold.

Don't Rush Things: I'm guilty of getting too far ahead of the dating game sometimes and I end up being disappointed if situations don't go my way. Life naturally progresses and dates or meetings with a person of interest should be the same. Sure there are those moments when you ask yourself "Should I go for the kiss?" and the situation will determine the choice, but the rules aren't always the same as each person is different. One day you might feel brave and the next you may not. Take the date or experience as it comes especially if being shy is limits these experiences. Maybe the 1st meeting will end early with a handshake but if you make a good impression the second might end with a kiss... or a home run?

Being shy should never be a disadvantage but should instead be the catalyst for working harder. You may have less to say but that just means they have more to discover.


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      pgrundy 9 years ago

      Great hub! You don't sound like a loser to me--you sound like a nice guy who hasn't met the right girl yet.

      You want to know what the ultimate prop is for meeting girls? A really cute dog---big dog, not Paris Hilton dog--dogs are chick magnets. I'm female and live with a great guy, so I don't need to to meet girls, but every time I walk our Malamute some woman just gushes all over him, and most of them are good looking too.

      Just a suggestion. You sound like you're doing pretty well already though!