You are pretty sure that he likes you and you really like him, so how should you initiate the first contact? A hug is an easy way to attempt physical contact with a boy without looking like you are trying too hard, especially since a hug can be interpreted as a friendly gesture, as well as a romantic gesture. It's important to wait and find the right occasion to try the first hug, so that it will feel natural and not forced.
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Develop at least a casual relationship with the boy first. You should at least know him well enough to be able to talk to him and hopefully engage in a little light joking before attempting to hug him.
Stand or sit near the boy. Try to manoeuvre yourself, without being obvious, so that you are near him and within touching distance.
Attempt to make eye contact with the boy and smile often. If he returns the smile and maintains eye contact, there is a good chance he is interested in you, as well. Even if he doesn't maintain eye contact or smile, he just may be shy.
Touch him once or twice lightly on the arm -- or if he's seated, on the leg -- while you are talking with him to see how receptive he is to being touched. For instance, tap him on the arm to point something out. Make the movement a natural extension of your conversation.
Wait for the right moment. A good place to try and hug a boy the first time is a sporting event, such as a high school football game. If something really exciting happens for your team, you can "spontaneously" reach around and hug him. Most first hugs will be from the side, placing one arm around his shoulder and squeezing lightly is usually the common way of doing this.
Apologise if you are a bit self-conscious or if you want to put him at ease. Pretending that the hug was an accident is one way of feeling out the situation. Say, "I'm sorry. I just got so excited by that touchdown," or something else that befits the situation. If he likes you, he will probably tell you that it was OK and that he liked the hug. If he didn't like it, he might move away and you can both pretend it was an accident.
Pretend you are cold. If there isn't a sporting event to watch and you are outside together, you can mention to him that you are cold. He may offer to warm you by putting an arm around you. Respond by putting your arm around him in kind and thanking him.
Drape an arm around him, like you would a friend. If you are hanging out with a group of friends, you can 'jokingly" put your arm around his shoulder if you think the moment is right. Just act like you would if he were one of your girlfriends and do it in a non-sexual manner. If he likes you, he may put his arm around you, too. What may start out as a friendly hug could slowly turn into an actual hug if he likes you.
Hug him lightly at first. Don't hold on or squeeze him in tight. You will make him uncomfortable. Hug him about your shoulder level or below. Hugging high up on the neck should only be done with a boy you are in a comfortable relationship with.
Watch your arm placement. If he is reaching toward you with one arm higher and the other one lower, you need to use the opposite arms to return the hug, so your arms won't hit.
Choose carefully the place where you want to hug a boy. In some schools, hugging or other personal displays of affection are not allowed.
Understand that in some cultures hugging may not be acceptable. If you try to hug a boy from one of these cultures, he may be turned off completely by your boldness.
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