From friend to boyfriend? How to make the transition?

Jonathan in Clinton, New York, writes, "I have many friends (who are girls) but no girlfriend. I hang out with them all the time and they seem to enjoy my company. What can I do to move from being just a friend to a boyfriend of this particular girl, Kelly, that I like?"

You have to understand that (most) women love men who can treat them as women - that is give them respect but also take charge. As a man it is perfectly fine to ask of a woman what you want. So for instance, it would be perfectly fine to tell Kelly that you find her interesting, she ignites your curiosity, she is intriguing, etc., and you would like to know her better. "What about we do something together?" You can always suggest something that does not sound like a date - for instance, a hike, a trip to the museum, cooking a meal together, etc. that might be of interest to her, of course, but is in a place where you can actually talk without too many distractions (movies and restaurants do not work). What is the downside? She might decline and if you perceive that it is very firm and she is definitely not interested, you have lost nothing. Actually you have gained something - you have gained the knowledge that you can take her off the list of potential girlfriends and move on to others. Since you did not necessarily suggest a romantic date, there is no reason not to continue to be friends as always.

Recommended link: Dating idea: Cook a meal together