I differ from what most contemporary literature says in regards to successful dating. Much advice I read refers to playing “The Game”. That is, ladies play hard to get and guys appear uninterested. Rules like “don’t call for three days after meeting” apply here and I know this style of dating works.

dating confidence

I don’t think it’s the best thing to do to improve your odds and it is a rather dishonest way to start a relationship. If you want a long-lasting, successful relationship, is feigning disinterest (i.e., telling a lie) really the best way to begin? I didn’t believe so. At any rate, a big part of some of the advice out there requires that pretending to be confident is a part of the game and is required for success…and I disagree.

Much of what I will talk about here builds upon my article Dating Multiple People (and Why You Should Be) and you may want to review that if you haven’t.

Comfort Over Confidence

A big selling point of the advice I read when dating online was that guys should just be “confident”. Often there will be exercises like talking to random strangers to build this confidence. If you couldn’t be confident, then just pretend! I was shocked how so many authors would write almost exclusively on this one topic, as if there was nothing else involved with dating.

I’ll tell you a secret: even though I had great success with online dating I was never all that confident. I became very comfortable with dating but I doubt anyone would have said I overflowed with confidence. And I think there is an important difference between comfort and confidence: confidence is more internal and about your personality where comfort is external and often about your surrounding or experience…that’s my take at least. The point is I never felt confident and abandoned the advice that said to pretend to be yet I had success once I became comfortable.

dating comfort vs confidence

If Everyone Gives the Same Advice It Must Be Right…Right?

All the books I read suggested I pretend to be confident (once again, suggesting dishonesty with first impressions). I hated trying to appear confident and assertive even though I wasn’t. It felt like a great big lie: I’m looking for a long-term relationship but I’m going to sell myself as something I’m not to find it? I tried to follow this advice anyway but like many other guys I failed in most cases.

However, as I dated more and more I became comfortable with the process. I was still nervous and I was still far from the most assertive guy but because I was comfortable with the dating I often appeared confident…and the great thing was I wasn’t pretending to be anything! I was making better first impressions without any lies or acting.

A Better Way to Improve Your First Dates (While Staying Honest!)

So, the best thing I believe you can do to improve your odds when dating is to ensure you are as comfortable as possible. The more comfortable you are, the more comfortable your date will be, too.

Remember: this has nothing to do with how confident a personality you might have. This is not about changing who you are. It is about removing variables that make you uncomfortable and about improving your skill in a particular area.

My advice: don’t put too much weight in literature that says being who you are – even if that means being shy – means you cannot succeed. I’m shy, I succeeded. Every book on the planet could argue being confident is the only way to success…I don’t care! I know otherwise.

So if you want to raise your comfort with dating to help improve your odds, here are my recommendations:

Date as Many People as Possible

For some people, the dating is uncomfortable because of how infrequently they do it.

I know a woman who will not drive on major highways near any major city. She drives on back roads and familiar highways all the time and, for all other purposes, has a normal degree of comfort with driving. If she were forced to drive on a major interstate it would be a terrifying event for her. I suspect she would drive poorly because she would be so affected by her fears.

lack of confidence or comfort?

I suspect that no matter how often she drove on that interstate she would always have some degree of nervousness. Yet the more she drove on the interstate, the more comfortable she would become at doing so.

This is how dating was for me. I was frightened I was going to mess up and it affected how I was presenting myself. A frightened driver will often drive poorly, even though they are erring on the side of extreme caution. The same goes for dating. The less comfortable you are the less likely you are going to represent yourself in the best light. The more you date, the more comfortable you can be at doing so, the more you are likely to behave as you normally would. There are many other good points for dating as much as possible which I covered before but if for no other reason, it should be done to increase your comfort.

Second Dates

Unless you are already comfortable dating, you should almost always try to schedule second dates…even if you feel like it won’t lead to anything beyond that. Again, this is about getting the experience to become more comfortable.

There are a few exceptions to this.

  • If it was a horrible date, don’t try going through it all over again.
  • Second, if you feel like your date really liked you but you didn’t feel anything in return, don’t lead them on.

Ignoring those cases, second dates are great experience because you should be moving beyond the introductory small talk. You’ve now met your date and, seeing that he or she wasn’t “scary”, are more willing to have a fun date such as bowling or miniature golf or meeting at a bar. Additionally, when I knew I had no intention of a third date, my confidence actually was through the roof on the second. I was there to gain comfort and to have a nice evening with a new friend.

Go on second dates!

The great thing about this high level of comfort is that it seemed to carry over onto other first dates I would have around the same time. Also, the more I dated the more refined my mental checklist for what I was looking for became. My top list of traits desired in a woman was drastically different at the end of my dating life than at the beginning thanks in large part to the number of women I truly tried to learn about.

One last plus to the second date: you’re not the only one who is nervous! Your date may have been so nervous on your first date that they represented themselves horribly. The second date gives them some confidence that you accept who they are and allows them a chance to show what they are really like. You might even find out that you like who they are on the second date much more than the first!

Oh, and looks shouldn’t matter that much, at least not for one more date! Don’t make this into something bigger than it really is. You may not like them solely because there is a lack of physical attraction but you’re not going to start a serious relationship – just have another night out. For me, lack of attraction was no excuse to avoid a second date.

Location

I think this is often overlooked but be sure to select somewhere you are comfortable.

Because I tend to be a quiet talker, I’ve never been comfortable at a bar. However, I tried meeting several girls at bars in my early dating days. I thought everyone meets at bars so I have to as well or I’ll come off as strange. Well, on those dates I came off a strange anyway so I found it better to just select a location where I could have a chance.

Location matters! Be comfortable...

Better to be comfortable at a diner than uncomfortable at the nicest restaurant in town. If the only thing your date enjoys is the location, chances are you’re not going to make it far.

Initial Meeting

When you initially meet, greet in a fashion that you are comfortable with. Don’t go for a hug if you know you’ll go rigid as soon as you touch. Handshakes can be…odd, but better a comfortable handshake than an uncomfortable hug. Immediately introduce discomfort to the date in the first few moments just to accomplish any modern dating ritual is counter-productive.

Any discomfort caused early in the date (and you don’t get earlier than those first few seconds) is hard to shake off. I am not comfortable with contact with those I’ve just met so normally if they approached me they might get half a hug (one arm around her shoulders briefly) but more often I would just jump right into conversation and make my first act holding a door for her.

A Plea To Those Uncomfortable with Dating

Recently, a friend expressed extreme loneliness to me and my wife. We began to talk with him about what he was looking for and discovered that he was a dating snob. He knew exactly what he wanted and anyone who didn’t fit perfectly to his list, well, he wanted nothing to do with them. Please do not approach dating this way.

You must date many people or be very lucky to have success online.

You must gain comfort with what you are doing. This may mean contacting people who you suspect will not last past two dates. This may mean occasionally ignoring the suspicion that there will be a lack of physical attraction. It may mean ignoring the fact that they smoke but you don’t. It means staying open minded and dating as frequently as your schedule allows.

If you approach online dating with an attitude of, “I’m only going to date those who are exactly what I want”, but then finally meeting this perfect person only to display enormous discomfort, you do yourself a great disservice. A child does not compose a piece after his first piano lesson. Do not fool yourself into thinking dating is any less complex and that you’ll just get it right. You should get out there and practice!

To put this all another way:

Bad Approach to Online Dating:
Searching for the perfect person and then dating them

Good Approach to Online Dating:
Dating as many people as you can allowing yourself to find the perfect person


Don’t worry about all the confidence talk. Gaining experience is far more beneficial than acting in my experience.