Hi Harlan,

I’m 30, attractive and single. I work for a small company (11 employees), and have developed a gigantic crush on one of my co-workers, who has become a really good friend. We hang out, play golf, get drinks regularly. We also talk about our respective dating relationships, etc., so we know a lot about one another. He’s almost everything I want in a guy. However, he’s seven years younger than I, and is my co-worker. Admitting any feelings not only could make things awkward at work (especially if it’s not mutual — which I tend to think it’s not), but also could lead to us potentially breaking the nonfraternization policy that our company has. Do you think I should just keep my feelings to myself? What should I do?

Support Girl for the Perfect Sales Guy

Dear Support Girl,

No sale! I wouldn’t go there. It could cost you your job. There are thousands of 23-year-old men who would want to hang out with an attractive 30-year-old. When you’re not hanging out with this 23-year-old, what are you doing to give men access to date you? How can these men find you? Whatever you’re doing, do more. Until you have another job or he has another job, I wouldn’t cross that line. There are too many other men and too many reasons not to go there.

Dear Harlan,

I am a sexually inexperienced college male. I have already completed two years at a big school, and have had little luck with women. Though I am in a fraternity and probably would be considered one of the more popular and outgoing guys, I have found that whenever I start to get close to a girl, even during a drunken night at a bar, I find that I let my nerves overcome me, and I tend to back out of the situation before things get hot and heavy. I basically spent my high-school years as the awkward kid, so I did not experience my first kiss until freshman year in college. I started to gain more experience, but as I slowly began to round the bases, I became more nervous. I have let my inexperience turn into a fear of being with women. I’m scared that I will not perform well, or will get too excited and experience a moment similar to Jim’s from “American Pie.” I’d like to find a girlfriend, but clearly my inexperience gets in the way. What can I do to overcome this?

The Inexperienced

Dear The Inexperienced,

Not all women want to hook up with a porn star (maybe a few, but you don’t want them). Instead of hooking up, try dating. Dating lets you get closer to a woman over time. It gives you time to have honest conversations. It helps you understand a woman’s past and what she wants in the future. Sex can come later — but trust comes first. Once you know a girl better, your inexperience won’t be the focal point. In fact, it will be a small part of a bigger relationship. Once you go on a few dates, bring up what weighs heavy on your mind before getting hot and heavy.

Harlan is author of “Getting Naked: Five Steps to Finding the Love of Your Life (While Fully Clothed and Totally Sober)” Write Harlan at [email protected] or visit online: www.helpmeharlan.com. Send paper to Help Me, Harlan!, 3501 N. Southport Ave., Suite 226, Chicago, IL 60657.