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.
Aside from their innate male tendency to overlook anything that isn't spelled out in black and white, shy men will by default doubt any sign of your affection.
That offense will reflect negatively on you and the relationship.
So be careful about how much (and which) initiative you take.
At most, it is a reliable source of advice for women who want to improve their chances with the opposite sex.
A post I made about why women shouldn't take the initiative in relationships evoked some questions about how to deal with shy men - after all, shy men don't chase women, and are unlikely to initiate anything.
Once this happens, you will need to gradually assume a less assertive (more traditionally female) role, because he will then be more liable to get bored with you, wonder if he could do better, consider his other options (the perception of which his newly-found confidence will likely inflate), fool around, etc.
If nothing else, this blog is an outlet for voicing my astonishment at the typical female's ignorance of the male mindset.[Read: Tips to reject someone who likes you] A friends with benefits relationship is always fun, as long as it lasts.Use these 25 friends with benefits rules to prolong the fun for as long as both of you safely can, and end it just before it’s too late.It’s too risky and you may get caught, especially if both of them are trying to exchange sly smiles and sneaky glances with you, or worse, trying to reach out to your crotch from under the table at the same time. Yes, you get to have a no strings relationship with someone. But keep that libido and enthusiasm down or you’ll end up getting bored or scaring your screw buddy away. You may be intimate with each other, but that’s no excuse to see each other in any place other than a bed. It’ll take the option of falling for them out as long as you’re infatuated by someone else. Don’t try to find out about their personal life or have conversations about life and its problems. As sexually attracted as you may be, avoid having sex with a good friend that’s good looking. Or end up having an affair when one of you is in another relationship and that can get really messy. [Read: Conversation tips to end a relationship] #13 Avoid anyone who’s seeing someone else.You’re into each other for sex and you really should avoid involving anything else. You will lose that friend or both of you will hate each other within a few months. It may sound sexy and wicked and even give you an ego boost, but you’ll get caught or one of you will have to deal with a heavy bag of guilt that will ultimately be shared in the open. Don’t talk about your personal lives with each other. If you’re falling in love with your friend with benefits or feel like things are slipping out of hand, you owe it to your friend to at least let them know the truth so both of you can decide the course of the relationship.If a girl doesn't approach or initiate contact with a shy man, nothing will happen.This is true, but handling this situation isn't as simple as you might think...But convince yourselves that the other person is actually dating someone else. [Read: Signs you’re more than friends] Things that can happen in a friends with benefits relationship As fun as a perfect friends with benefits relationship could be to begin with, it does have a few bad sides too.I’d like to tell you that you can avoid any dark corners, but at some point of time, the bubble always has to burst. You lose the chance of falling in love with someone who may be perfect for you. As much as you may try to pretend like you don’t care, you may be upset if your friend dates someone else. But it’s something to be wary about, especially if your friend has a lot of active friends with benefits.You may take a while to realize it, but even if you think your sex friend is the most charming person in the whole world, you really can’t do anything about it because it’s too late to retrace your steps. If one of you have been hasty or made a few wrong decisions, both of you can’t do anything but walk away forever. And all this even though you know the ground rules. And of course, you’re not going to talk about it because *you don’t care*, right? Romance always finds a way to crop up for one of you if the relationship lasts more than a few months.And trust me, both of you aren’t going to like where that road goes. ] Things to remember to prolong the relationship safely #21 Are you slipping? [Read: Signs to find out if you’re in love or lust] #22 Poke into the details. At the end of it all, as fancy as it sounds, a friends with benefits relationship is almost always too good to be true.