This initially came up when a guy I know had yet to go on a date at the age of 21. He said he didn't know how to ask this girl out he went to college with that he had been talking to now and then both in person and on IM. He didn't know how to tell whether or not she was interested in him. Now, the only advice I could give would be that which I thought would work on me, but most women seem to think that what will work on them should be applicable across the board. However, I did run this by another male friend of mine and he seemed to see my suggestions as fairly good ones, so I thought I would pass them on if anyone is interested.
Most guys who haven't had a girlfriend when everyone else had them, from my experience, are genuinely good guys. They want to be accepted, and they want to show respect for the girl they're into. When you're interested in a girl and you have set up even a casual friendship with them, there is still that awkardness of physical contact, and the guy I spoke to didn't want any gesture from him to be taken the wrong way. I told him that the best way to test a girl's dance space is to make a gesture toward a common area of her body. When I was student teaching, I was told that the only areas of my students' bodies that I should be touching were shoulders and heads (I was teaching at the high school level, but I would say this could apply to even elementary and secondary levels). The same can be said for girls. Here are some suggestions I gave for casual contact:
- Pay attention to her earrings, if she changes them often, if they dangle, if they are in any way eye catching. Though it may seem gay, compliment her on her earrings, reaching up to touch her ear with your fingers. Most women are glad to show off their jewelry and will note what you notice about them, and they may even lift their hair up or lean their neck closer to you so you can see her earrings better.
- The same can be done for rings, plus it gives you an excuse to hold her hand. I would avoid the same gesture to necklaces, however, no matter how short the chain is.
- If her hair is long or is sometimes in her face (assuming she's not using gel or hairspray, in which case she may not want her hair to be touched), a slight gesture to pull a strand of hair behind her ear for her is another way to test the comfort level between you.
All of these are mainly used to see how comfortable she is with your touch on non-erogenous zones. If she winces or pulls away, that doesn't mean she is scared to be touched, but it will cause you to be more cautious. If you can avoid making assumptions from as simple a gesture as these, you're on the right track.
Massage is something that is often misused when flirting with a girl, because most men go for the shoulders and back. That's all well and good, but if she is uncomfortable with you touching where her bra hooks together, she may push it aside during the massage but still harbor a little edginess afterward. I would suggest hand massages, and I have suggested them to every guy friend I know. I also tend to give hand massages to guys I like because it requires less involvement and time, when I don't necessarily want an invitation for a guy to take his shirt off. We store a lot of tension in our hands and giving a hand massage gives a better opportunity to show off how strong your hands are than a back massages, since there are fewer and smaller muscles to figure out, and almost anyone can give a good hand massage. By the same token, I would hold off on foot massages until you are more officially a couple, for the obvious reasons.
Again, I may not be adding anything new to the advice column for women, and if I haven't, please msg me and I will remove it. | 
