How to Date Multiple Guys Without Being Shady or Called a Cheater You may be interested in knowing how to date multiple guys, but you don’t want to hurt anyone’s feelings. Good news-just follow these tips. Learning how to date multiple guys without being shady isn’t as hard as it sounds. Haven’t you seen Sex in the City? Samantha is all about no-strings-attached dates with multiple men. I was the same when it came to dating. Okay, not the same, but I wasn’t committing myself to anyone. Sometimes I would be dating a couple of different guys at once. I was feeling them out and seeing which one I connected well with.