—It Takes Two
To put it in less sitcom-y terms, you have my hearty approval to date two dudes at once. In fact, it's practically a rite of passage these days, especially if you're a U.S. senator. Anyone who's ever been to a dueling-banjos night will tell you when it comes to teeth, four is all you really need. Wait, no, it's that two is always better than one. The same logic applies to casual dating, and here's why:
It lowers the pressure for all of you. We all know from reading Cosmo that guys—like horses and small children—spook easily, so the best way to avoid scaring them off is to not be way too into any one person too soon.
Less pressure is good, especially in casual situations when you're on the fence about someone, as you seem to be with guy No. 1. It's easier to discern what you want when you have more than one option in front of you. Why else would the Hometown Buffet franchise thrive? It's not the creamed corn surprise, I tell you.
Also, it's dating, not, like, signing a 30-year mortgage. There's no need to be exclusive while you're getting to know people. Besides, unless you have that "let's go steady" talk over malted vodkas, the assumption is that you're dating around. I do think that honesty is important in scenarios like this, especially if you're sleeping with more than one person (more on ethical sluttery here). This doesn't have to be some big confession, unless guy No. 2 is guy No.1's brother or you're on "The Real Housewives of Cook County" or something.
In regards to fear of double booking, dating more than one person shouldn't be any more challenging than having access to a day planner. If you have the wherewithal to schedule both a dentist AND a gyno appointment in the same week, you'll be fine.
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