Of course, he will question this over and over in his mind, wondering whether you were asking him to hang out just to be friends, or if you wanted something more.
So show him that you want something more - ask repeatedly.
I’m young and I want to have fun, out in the world, not be tied down to someone’s living room while her kid sleeps in the bedroom. I admire my friend for being a stand-up guy and taking care of his son, so my opinion of a woman doing the same … Also, her ex had issues with me being around his daughter because he was threatened by the relationship that was forming.
Also, my friend’s ex had a kid that always wanted to sleep in his mom’s bed and that would be a problem for me. I want all the perks that come with a grown-up relationship.” “A lot of my friends are divorced and one guy even has a kid after a one-night stand.
His masculine instincts will kick in, and in some cases you can end up with a man that acts towards you the same way that a confident man would have acted from the outset.
So, if you do choose to initiate, do so only during the early stages of dating, that is, until he builds his confidence and comfort around you.
The first thing to do when you find yourself attracted to a shy man is to question your feelings for him.
In other words, ask yourself "Am I attracted in spite of or because of his shyness? A very close friend of mine is extremely shy, and I know plenty of other guys that are shy. Shy guys, almost by definition, do not have the balls to initiate and pursue women.
I went out with a girlfriend in Montclair, NJ, to a fun place called Just Jakes. It was a little deceiving, sure, but I thought telling the guys I was a single mom would influence their answers—and I wanted raw thoughts.
It was lovely being out sans Jack, having a cold beer at the bar, surrounded by other adults enjoying drinks, conversation, and music. I videotaped their answers, transcribed what they said, and here’s what I got: “My mom was a single mom most of my childhood, so I have tons of respect for single mothers.
In general, you will need to carry the relationship up until the point that it is "official." When it has been established (or is otherwise clear) that the two of you are together, then you should start reducing your initiative and letting him take the reins.
As I said, he will probably start to do this on his own anyway, so rather than forcing it, just be cognizant of the transition.
Unfortunately there is no quantifiable or simple rule here, as his threshold for embarrassment will vary in proportion to his shyness and his pride, which are different in every man. Well, for starters, in the early stages, you will need to give him blatant signs of your interest.