If u can tell me that when u were new to meeting women in this game or any other, that you didn't get make a mistake or get taken advantage of, then u are my Hero... asking If this guy has low self Esteem because he spent a few extra bux is pretty disrespectful. I've spent plenty of money in the past and think that generosity and kindness are huge indications of self esteem and good character. The guys that get down on other dudes for their generosity and kindness are really the folks that need to look in the mirror and reevaluate.
Perhaps u are a great dude too..And if so, take a step back and realize that what u consider a weakness could be a true sign of a great person...
Cheers man.