Dear Anon-O-Box: Shy Guy Afraid of Dating Sites

Dear Anon-O-Box,

I’m terrified of dating sites.  Well, not so much “terrified”, as they make me really uncomfortable.  It just feels like every time I’d meet a person there, all our conversations/interactions/etc would have a feeling of “you are expected to form a relationship with this person” hanging over them.  I don’t know how to put it better, but it feels like there’s this glaring expectations of how I feel about each person.  I don’t really know that I could easily form a relationship when it feels like everyone in the room is watching me or something.  Do you have any advice about how I can get over it, other places online that I can go (there’s never any sort of con nearby), or something else?  I’m a straight male, 22, and also signed up for your newsletter.  Thanks!



e answers:

Dear Shyguy,

As a shy girl, I have a bit of advice for you. Being shy is entirely not worth it. Sure, you’ll save yourself a little bit of heartache when you fail at things – and you will fail – but it’s the failing that makes you into a better, stronger, awesomer person.

The good thing is that the internet allows us to meet people and interact with them while still in our comfort zone. You’re in your own house, on your own computer, and you have a backspace key handy. You can breathe. You can take things at your own speed. Awkward silences are much, much less awkward. You can “brb” if you need to take a quick walk to collect your thoughts.

Online dating is a boon for the shy guy or girl

The expectation you feel of “I have to start a relationship with this person” is not an uncommon feeling, but it is misplaced. When someone comes in for a job interview, a manager doesn’t feel bad about talking to them and then not hiring them for the position. It’s part of the process to talk to many people and find the one with the best fit. In online dating, you’re simply talking to someone and getting to know them better. The relationship part doesn’t start until after you’ve met in real life.

Since you seem to be a bit green (and I mean this is a nice way!), let me tell you a bit about some of the many clients I’ve worked with over the years I’ve been helping geek singles find love.

Very few relationships start immediately after the first date. And by very few, I’d say 2%. 2 out of 100 first dates turn into immediate relationships.

Clients will come back after a first date and say, “Y’know, I really liked that person and I think I’m going to meet with them again later this week.”  And they do. Sometimes it pans out into a relationship and sometimes it doesn’t. Sometimes they end up with a good friendship.

Or they come back and say that it didn’t work out that well. There wasn’t a click. I help the client craft a nice “Thanks, but no thanks” email and we go back to the drawing board.

The best part, shy guy? If things are going well on the first date, you can use that comfort zone of the internet to send messages and start conversations that you’re too shy to start in person. As you get more comfortable with your date, your shyness will evaporate and you can communicate more and more in person.

Alternatives to online dating

I will stand by my statement that online dating is the best way to go if you’re shy.  Why?  Because the alternatives I’m going to list below are even more outside the comfort zone of your typical shy guy/girl.

It’s Just Lunch: A matchmaking site for professionals. You sign up for their service and they’ll hook you up with a lunch date with another single person that they think you might like. You have lunch on a weekday (just during your hour lunch break) and afterwards, you each tell It’s Just Lunch how it went. If one person isn’t interested, the match is discarded, but if you both say yes, they’ll get you connected outside of lunchtime.

Table For Six: A group spin on It’s Just Lunch. Table For Six sets up a dinner party for three guy singles and three girl singles. A host or hostess from TFS will introduce you all to each other and get the conversation started. You get to know one another over the meal and then give your feedback to the host. Again, if there are mutual matches, you’ll get the person’s contact information so you can meet up for a one-on-one date later.

Meetup: Check out Meetup for singles groups and specific interests groups in your area. Want to brush up on your French? Go to art museums? Play Warhammer? There’s a Meetup for that. Not everyone you’ll meet will be single (unless it’s a singles-only group!) but it doesn’t hurt to expand your social circle and practice chatting with strangers.


*hugz!*  Overcoming shyness is hard work. I struggle with it on a daily basis, so I know. But I’m also proof that you can do it. You can get into the dating scene and find people that you’re compatible with and when you do, it’ll be worth all the hard work.

Happy dating, geek friend.

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