I’m not a gambler because I have a real resistance to losing my money. The systems are set up in the house’s favor. However I (I’d guess everyone else) would be happy to gamble if only playing with the house money. The reason being is that it is extremely easy to bet when you have absolutely nothing to lose.
This same phenomena applies to the dating world as well. From my own experience, when I was single, I found it almost impossible to get someone interested in dating me. However whenever I had a girlfriend, I seemed to have no shortage of interested people. Now part of this may be attributed to competition/supply in demand but I think one of the key factors is “playing with house money”. It was always easier to make conversation and flirt when I already had a girlfriend because I had nothing to lose. Rejection was impossible.
This creates a bit of a paradox because in order to “play with house money”, you need to have a significant other. Not actually, the key component to “playing with house money” is a true belief that you have nothing to lose. The fear of rejection that you feel is a feeling that you created. How can you make the possibility of the date valuable and make the rejection worthless?
The way to make rejection worthless is to break it down into what it truly means. The person that you have approached is not rejecting you. They are rejecting their perception of you which may be way off from reality. A rejection is not a finality, it is a learning opportunity. As with anything else, improvement requires a degree of failure. Since we don’t have virtual reality simulated dating programs (yet), you need to take these experiences head on without fearing rejection but fear of the loss of opportunity. I cannot think of a time in my life where I regret telling someone how I felt about them. However I’ve definitely got a few examples of regretting the fact that I didn’t tell them.
You’re playing with house money. Someone saying yes or no to you does not change your value as a person. Your worth is decided by one person and that is you. The only way to lose that money is if you decide to give it away.