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Making Your Approach
Make her feel special. When you see the girl, say hi, make eye contact, give her a wave, and start talking to her. If it's your first time holding hands, then you may both be a little nervous, so it's important to put both of yourselves at ease first. Though holding hands is an innocent gesture, it does come with a level of intimacy, so you should have a good sense that the girl likes you before you go make the move. Even putting your arm around her or putting a hand on her knee can be seen as less intimate than actually holding hands, so try initiating other innocent physical contact before you hold her hand first.
Get closer. If you're sitting, just place your hand down about an inch away from hers. This can help you get a read for how ready she is to hold hands -- if she moves closer to your hand, then she's probably ready for more. If you're standing and walking together, try to get closer to her until your hands are just inches apart.
Make contact. You should make some physical contact before you go ahead and grab her hand. If you're standing, put an arm around her shoulder and brush against her arm until you reach her hand, or keep walking and gently "accidentally" touching hands until taking her hand in yours feels natural. When you're ready to make contact, you can choose from a variety of ways to hold her hand. Try to be as relaxed as possible before you make contact. The more nervous you are, the more likely you'll be to have sweaty hands! Of course, this is not the worst thing in the world, but if you can avoid it, that's great. Be as direct as you can instead of fumbling for her hand.
Don't be upset if she's not into it. Contrary to what you may think, not all girls love holding hands. If she pulls away because she's not interested in you, then you'll get the message pretty fast because she'll pull away with her entire body and will look generally uncomfortable. But there's a good chance that she's just not into holding hands because she thinks it's corny or because she's nervous that she has sweaty hands or something, so don't worry too much; you'll figure it out eventually. If she doesn't want to hold hands, try making a joke to lighten the mood. This way, things won't feel as weird afterward.
Mastering Hand-Holding Techniques
Slide your hand under hers. This is a bold and effective maneuver. If you're nervous, let just the edges of your hands touch for a bit before you go in for the kill. Just slowly and gently slide your hand under hers so that her hand is on top of yours. You can move your hand around a little bit to gently play with her fingers. This works great when you're sitting down.
Place your hand on top of hers. This is another intimate technique. Just move your hand so that it is over her hand and gently pat or touch her hand. If you feel more comfortable, you can even give her hand a few gentle squeezes or even a massage. This can be a great hand holding technique if you're sitting at a restaurant or even watching a movie. It doesn't get as tiresome as holding hands when you're walking can get, because you can just relax and rest your hand on top of the girl's.
Do the palm-to-palm. This is a common way to hold a girl's hand. Just move your hand so that your palms are facing each other. You can even gently caress her palm if you're sitting down and feeling more playful. You can do this more relaxed hand holding move before you fully clasp hands.
Clasp hands. After you touch palms, you can intertwine your fingers, fully clasping hands. This can work whether you're sitting down or standing up, though it's probably more typical for couples that are standing up and walking. You can hold her hand passively, just clasping it, or caress her fingers a little bit. If you're walking while holding hands and are feeling playful, you can even swing your hands back and forth a bit.
Hold pinkies. This is another flirtatious and fun way to hold hands. Simply move your pinkie towards hers and lock pinkies. This is a fun one because you can pull apart or get closer together and just be playful with one another. You can also try this one when you're walking, which can be fun if you're swinging your hands back and forth a bit. You should probably wait until you're more comfortable holding hands the regular way before you make this move, though.
Becoming a Pro
Know that it's okay to take a break. Once you start holding hands, you aren't required to spend the rest of the evening, the walk, or the movie doing so. It's okay to take a break, whether it's because your hands are sweaty, your hand is getting tired, or because you just feel like it. Just break contact off gently instead of abruptly dropping the girl's hand, and you'll be fine.
Mix it up. You don't have to clasp her hand, clasp pinkies, or put your hand on top of the girl's the whole time. Mix up your hand holding techniques so you don't make the girl feel like she's holding a limp fish in her hand. Stimulating her hand too much can make her feel too frenzied, but just letting your hand sit there can make hand holding feel about as romantic as studying for a Geometry test, so find a balance between caressing her hand, not caressing it, and moving between different hand-holding techniques.
Kiss her hand. If the hand-holding is going great and you and the girl are really hitting it off, lift her hand to your mouth and kiss the back of her hand. You can even make eye contact when you do it for a more intimate touch. This is a very romantic gesture, and you should use it sparingly. But if you do it at the right time -- like at the end of a nice hand-holding session -- it will really make her like you!
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