Using a Two-Arm Front Hug
Get close to the girl you’re hugging. Since in this method you’ll be approaching the girl facing forward, it will be easier to gauge where on your body her height reaches. Especially with a forward-facing hug you’ll want to be sure her head doesn’t end up right at waist height or lower. For the forward-facing hug you’ll want to bend so that her head can meet your shoulder, or at least your lower chest.
Bend at the waist and put your arms forward. As mentioned, bend enough that your chest is at the height of her head. Bring your arms forward in front of you and let her come the rest of the way. This way it will be her decision whether to place her head into your chest or into the bend of your neck. Fold your arms across her upper back as you would with any hug. Avoid placing them around her neck instead. Keep your head facing forward. Don’t turn it to either side, as you might bump heads or breath in her face once she comes close.
Stay bent for the duration of the hug. Some might make the mistake of thinking they would only bend at first to begin the hug and place their arms, and afterwards relax their pose. Better instead to stay bent for the short time of the hug. Trying to straighten your back will just end up in some awkward movement while you try to stay in the hug.
Release after a few seconds. Again, the length of any hug will simply depend on your relationship with the one you’re hugging. For example, if this is your first date, you wouldn’t want your hug to linger too long. When you’re hugging face forward, you’ll want to release and step back first as the tall one. Since you’re 'surrounding' the girl you’re hugging, you’ll want to move your arms out, straighten your back and step backwards.
Using a One-Arm Side Hug
Approach the girl you intend to hug from the side. This will almost certainly be determined by how both of you are standing. Most likely you’ll already be oriented in a certain way to one another, so it won’t be a matter of choosing a side to hug. As the hug is beginning, you’ll need to step close to the girl in question. As you get close, move the arm that will be used for the hug (it should be the arm closest to her) out to the side of your body. Begin to position it horizontally in anticipation of the hug. Wait until both of you have sides touching before placing your arm on the girl you’re hugging; keep your arm out to the side instead. One of the strongest advantages of the side hug is avoiding the girl’s head being pushed directly into your waistline or lower, which can be embarrassing for everyone. While the side hug alleviates this issue, you still might consider bending if the girl is still at or below your belt line.
Tighten your arm with your hand at her shoulder. Once you’ve both come close and are against one another, position your arm around her so that your hand rests on the shoulder opposite you. Be sure to avoid placing your arm or hand on or around her neck. Keep your arm above hers. If your arms criss-cross in the hug, they can tangle and heighten any awkwardness. If you do bend down, it will be best to do so from the knees when in a side hug. Bending at the waist will create a difficult angle for the girl to put her arm around you. Whatever the height difference, the mid-waist and shoulder are really the only acceptable places to rest your arm and hand. You’ll always want to avoid placing your hand(s) at their chest or neck/head. One will end up feeling a bit awkward while the other is uncomfortable.
Embrace for a moment and release. A concern for any two people hugging, deciding how long to hold the embrace will simply be a matter of how close the two people hugging are. Conventional wisdom would suggest holding the hug for no more than three seconds for anyone who isn’t a romantic partner. As the tall one in the hug, don’t rush to remove yourself from the hug to avoid any awkward bumping. First relax your arm and move it away from her body. Let her back up and return to standing before you do the same.
Avoiding Pitfalls
Don’t make it awkward. You don’t have to apologize for being tall, and the girl you’re hugging doesn’t have to apologize for being short. There’s no need to say “Guess I’ll need to bend down” or “Sorry I’m so short.” Two people hugging will always recognize the size disparity between one another. However, there’s always room for some playful honesty in moments like this. It won’t hurt to be upfront and say “Okay, how would you like to do this?”
Don’t just stand there. Plenty of guys might overthink the situation and wonder if it isn’t better to just allow the girl to position herself however she’s comfortable and let their own arms rest wherever seems appropriate. This, however, isn’t really fair to whoever you’re hugging. Be sure to be proactive at the start of the hug. As suggested, be sure to bend down if hugging from the front or move your arm(s) out when hugging for the side. It’s not a terrible instinct to allow the shorter person to position themselves, but you need to meet them halfway by doing some positioning yourself.
Keep your arms away from their neck and head. In either a side hug or a front-facing hug, your arms may very well be at the level of the shorter person’s head. Since when two people of equal height hug they simply put their arms forward, the instinct is to do the same with any other hug. As you can imagine, having your head squeezed doesn’t really constitute a great hug.
Don’t lift her up unless she asks. Unless the girl you’re hugging is your significant other, don’t assume that just because a girl a short and you’re tall that she'd like to be lifted into the air. Some might assume it’s a playful and comical way to address the height difference, but it can quickly turn into an uncomfortable experience for the person you’re hugging.
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