Really, by the end of three dates you should know whether you think this could turn into something serious. There are specific things you should ask if you don't think you really know if they are worth dating. This is for your sake before you waste more time on a dud.
- How does he handle his debt? I realize money isn't really something that comes up in polite normal dating etiquette, but I'm challenging this rule. If you can manage to ask some questions without being too invasive about how he handles money the better off you will be. I mean do you really want to pursue someone who can't manage their money?
- What is his career like? If you are someone who pictures the perfect evening as cuddling up to watch your favorite TV shows before bed and they work two jobs... that won't work. By the third date you should have had plenty of time to get past the typical "I hate my boss" and "I need to make this merger by Tuesday" bit. Ask them about their life schedule and what a typical evening is for them, that should tell you whether to hit the pavement for a better match.
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