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Q: I was in a relationship for 8 years, now broken up. Recently I've noticed this girl at work who smiles all the time and makes me feel good. When I say hi to her, her smile gets bigger, but I can tell she is shy. She is only 17, so right now I would like to become her friend, and then maybe date later. My question is: How can I approach her without scaring her away and simply ask her out to hang out with me? -- Thomas, 23

Dr. Susan: I can think of a couple of non-scary ways to gain the interest of a very young woman you work with. You could sit near her when you eat lunch, or very casually offer her a cookie or some other token that can't be misconstrued as a major come-on. If you've noticed she likes cats, for instance, you could pick up a cheap cat-related keychain or other knick-knack for her. Don't wrap it or make a big deal out of it. I wouldn't actually ask her "to hang out" with you, since this isn't high school and you're both there to work. It's probably going to be best if you take every opportunity to make casual conversation with her and enjoy that smile of hers. Ask a question every now and then so you can get to know her better. It takes more than a smiley personality to make things happen. Take it slow, and don't try three different approaches all in one week or you will scare her away.