Hugging Him Romantically
Start the hug with a gentle touch on the arm, eye contact, or a smile. Whether you're in love or just dating, there is really no wrong way to move in for a hug. So just do it! A casual touch can be used to introduce a casual hug, and an intimate touch can be used to introduce an intimate hug. Let your hand brush against his arm a few times, or allow it to linger there for a few moments. Look into his eyes, or sneak up behind him and plant one on him. If you want to give him a hug, just give him the hug.
Wrap your arms around him. Don't overthink it, just wrap him up. In general, you'll slide both arms between his arms and his torso, connecting them around his back for a deep, close embrace. However, if you're feeling romantic, there are plenty of other ways to hug him: Wrap one hand behind his back, just above his butt. Place the other hand around his neck so that your fingers rest where his neck meets his shoulder. Lightly grab onto the left side of his neck (his right side) with your left hand. If you're extra romantic, you can lightly tousle the back of his hair with your fingers. Place one palm lightly on his upper chest, wrapping around his waist with your other arm.
Press your upper body into his. As you wrap your arms around his neck or chest, press your upper body into his. Pressing your chest into his is considered a "heart to heart" hug. If you're the same height as him, you might rest your head on his shoulder. If you're shorter, turn so that you rest your cheek on his chest. If you’re taller, try to lower your head so he can see you better and feel like he is in reach to kiss you.
Relax your body and fold comfortably into his arms. Just slow down and relax. A hug is simply a chance to press close together, enjoying each other's company. If your first hug position isn't right, simply move your arms and body into a more comfortable position. If you are in a good embrace, let your hug linger until the moment passes or you feel him begin to pull away.
Press up even closer to him if you want to turn up the temperature. Pressing your upper half into his can indicate romantic interest, but it is still fairly tame. Allowing your hands to roam or your legs to intertwine, however, is a great way to kick it up a notch and suggest stronger desire. Massage his back, neck or chest lightly with your fingers to kick things up a notch. Pull his face down into a kiss if it feels right, or if you're both looking for more than a hug.
Gradually ease out of the embrace when it feels right. Instead of stepping back and immediately breaking contact, take a half step out of his embrace and allow your hands to linger on his shoulders or chest. Look each other in the eyes and smile, or slide back in for a kiss. If you feel him slightly pulling back from the hug, don't try and grip him tighter. Follow the mood and ease out as well. There is no right amount of time to hold a hug, so just feel it out and enjoy yourself.
Hugging Guy Friends
Make eye contact and open your arms before moving in. You don't have to be dating someone to give them a good, warm hug. However, with guys you aren't romantically involved with, you generally need to give him a little heads up. Make eye contact, smile, and open your arms up. Unless he firmly sticks his hand out for a shake or seems to shy away/avoid eye contact, just move into the hug. Be flexible -- if he doesn't seem to want a hug, don't hug him. If he does, or you're unsure, just be yourself and do whatever you want. Very few guys will complain about a casual hug.
Open your arms and take steps toward him. You'll end up close enough that you can comfortably get your arms around each other and touch chests. In general, your feet will be 6-8" away from each other, but don't worry about it too much. It is a casual hug, so just be casual about it. Unless you're pressing your entire body into his and pulling him in close, you're not going to send the wrong signal. Open your arms as wide as you feel. You can feel free to open your arms wide if you want a big hug. If he doesn't seem like he wants a hug, you could give him a side hug. Move so you are side by side with him, and put your arm around his shoulder. This one-armed hug can get you out of many awkward moments if need be.
Slide your arms under his if he's taller than you. Just make sure your head is going the opposite way of his head and you'll be fine. If you're the taller one, let him slide his arms under yours. This isn't a hard and fast rule, of course, but in general it is easier to slide into a hug if you don't have to reach down to get under someone's armpits.
Wrap your arms all the way around his back. Once your arms are positioned in response to his, move them all the way around his body and gently but firmly embrace. Keep your body relaxed while you are putting your arms around his body. Your hands can be open and touch his back or shoulders, or you can clasp your own hands behind him. Don't think about yourself too much while hugging. This can make you feel awkward. Instead, concentrate on the guy you are hugging and try to enjoy the moment. Just laugh if anything goes wrong or feels awkward. Hugs are not complex signals or mating rituals -- they're a pleasant way to greet someone. Don't overthink it!
Embrace him warmly and briefly. To embrace warmly, try to think about him and not yourself, enjoy the moment, and give him a firm but gentle squeeze. A good way to think about your timing, if you're extra worried, is to just exhale into the hug, relaxing your muscles as you do, then stepping back gently once you're done. This will give you a good 2-3 second hug.
Step away, re-establish eye contact and smile again. Ease gently out of the hug and step back -- he'll do the same thing 99% of the time. You want to be outside his personal space, but don't move so far back that it seems unnatural -- one or two smalls steps is fine. Looking at him again will cement the good vibes from your hug so that you both leave the hug feeling great.
Knowing When to Hug
Look for open arms and body language. There are few more common, and more awkward, social moments then the debate between a hug and a handshake. One of the best indicators is someone's hands. If they extend their right hand towards you you can be pretty sure they want a handshake. However, if their hands move out, opening up their torso, there is a good chance they're expecting a hug.
Use a simple one-armed handshake to adjust an awkward embrace. If you end up stuck between a hug and a handshake, simple wrap one arm around the lower back for a one-handed hug. Lean in so that one of your shoulders touches his, but don't feel like you need to really embrace him if you don't want to. You can keep some distance, or angle your body away from him to keep things casual. This is a great way to end an awkward "what should we do" moment. Just wrap the arm, hug quickly, then stand back.
Take charge if the guy seems awkward or unsure of what to do. There is no reason why you can't stick your hand out or simply move to a hug if you want. Without fail, the guy will adapt to you, so just take the initiative and move in however your feel comfortable. Just make eye contact and go for it-- there are very few guys who do not enjoy a hug from a woman. That said, there are times when you're better off sticking to a handshake, such as: Buisness or professional settings. The first time you meet him. When you are unsure about his boundaries If you do not know/feel unsure about local or international customs.
Skip the hassle of a hug altogether and use different, more casual greeting. This can demonstrate a sense of ease or camaraderie. For example, you start with a quick wave, a high-five or a fist bump. This sets a casual, platonic mood between you and him. You could start with a high five before drawing him into an embrace, or you could playfully give him a light punch or fist bump on the shoulder. If he smiles, makes eye contact, and seems at ease, you can always move in for a hug when you say good bye. A quick wave and a smile from a distance is often a good way to gauge if they want a hug. If he responds warmly, just move on it.
Avoid hugs you don't want with a smile and your hand firmly extended. If you know someone is a "hugger," or you just don't feel like a hug is appropriate for any reason, take charge and stick your hand out early. Make eye contact and smile, then give a firm handshake. In the rare case that a guy seems extra persistent, you can try to guide his hand to yours with your free hand, making it extra clear that you want no more than a handshake. If you really, really, don't want to hug them, give your best smile and say something like "It's great to see you, let me shake your hand."
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