Does he feel the same?

This guy and I spent some time together and fooled around a little. Now I don't know whether to ask if we're an item or not. I've developed feelings for him but I'm worried that I'm setting myself up for a disappointment if he doesn't feel the same. What do you suggest I do?

If you're worried about setting yourself up for a disappointment then don't put yourself in the firing line until you feel more confident. He knows you like him. 'Fooling around' with him was a clue. Actions speak louder than words.
A man is like a shy Springbok. Make a sudden move in its direction, and it will bound off as though startled by a predator. Come across as non-threatening and it may feel safe enough to wander into your territory.
Take the focus and energy off him and apply it to yourself rather. Spend time with your girlfriends. Pamper yourself with a pedicure or a good hair conditioner. The better you look and feel about yourself, the more self-confidence you will generate.

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