Dear Thomas,
Two weeks ago I met a 55-year-old, highly successful senior executive and 8-years divorced man on a reputable online dating service. He is my second romantic interest I met online and the first one I will actually meet in person. I am a 51-year-old that looks 37, never-married, single woman who has not dated since my late boyfriend passed away 3 years ago. I am a little cynical about most men.

My new man has given me his contact information but not where he works, and he wants to come visit me. He might be protective of his privacy since he is a high-ranking executive, or there may be another reason.

How do I ensure my personal safety with a man I never met before? How do I ease my nervousness so I do not talk excessively so I can listen and hear? I want him to know I am not there for casual sex--how do I make all of these points and still keep his interest?
--Jennifer

Dear Jennifer,
My main concern about your first date with a man you met online is your physical safety, should you accept his suggestion of a visit/date. I strongly recommend that you meet him first in a public place, perhaps bringing a friend of yours with you. At the very least, tell a good friend when and where you are meeting. You can find good and extensive advice about safe online dating in many places on the Internet—start with this Beliefnet piece.

For your emotional safety, you might consider that an online meeting doesn't have to be followed by instant intimacy or a sexual relationship. You could take advantage of email as a good way to converse for a while. Even then, of course, you have to be careful: the person may not be telling the truth. You could turn your cynicism, not a very positive emotion, into intelligent caution.

You're clear that you don't want casual sex. If you continue to exchange emails, you can let him know how you feel about it. You can be clear and brief and then go on to other things. If you're worried about the sexual part and don't say anything, it will be the elephant on the screen and may interfere. A man worth knowing shouldn't be put off by a brief, clearly stated expression of how you feel about sex.

You say you don't want to put him off. That sentiment puts you in the down position, trying to please and not offend. It would be so much better to be equals from the start. Be yourself and let him make his choice of where he wants to go from here. Don’t be desperate. There are a lot of good men out there.

Good relationships can come from online dating. On one hand, online dating has pitfalls, chiefly the opportunity to hide and not show your true self. The beauty of online conversation, on the other hand, is that you can learn much about each other before you meet. You can pick up a very old and useful tradition of writing letters as a movement toward intimacy. Take advantage of this benefit, and be strong, assertive, and clear.

Your nervousness probably comes from not being confident about your attractiveness as a person. You're worried about the impression you make. The solution is not to hide your thoughts and feelings, but to present them with confidence. If this man is someone worth pursuing, he will be further attracted to you because of your strength as a person. Think about what you want from a relationship, and then don't back down.
--Thomas