How to Hold Hands
If you want to hold hands on a date, start by looking for subtle signs that your date is interested in holding hands, like grabbing your arm or playfully pushing you. You should also wait for a private time, like when you're sitting in a movie theater. Once you feel the time is right, reach out and gently take the other person's hand. To make it feel natural, carry on talking if you're in the middle of a conversation. However, don't make an issue of it if your date pulls away, since they may not be ready to hold hands just yet.
Gauge the level of interest. If you're out on a date, look for subtle signs that they might be ready for you to hold their hand. If your date has been giving you the cold shoulder all night, this is a sure sign that they are not interested. But if they have been walking close to you and seems comfortable, this is a good signal for initiating hand holding. If your date has found little ways to initiate gentle physical contact, like playfully pushing you or grabbing your arm, they are more than likely open to holding hands. Check your hands. You might be a little nervous, so check your hands to make sure they are not sweaty or clammy. If they are, subtly wipe them off or stick them in your pockets for a moment to dry them off. Your date may be nervous too, but sweaty palms are not very appealing. Also make sure your hands are clean and moisturized. Super dry hands or hands that smell are an even bigger turn off than sweaty hands. Wait for the right time and place. If you are in the middle of dinner or are doing an activity that requires you to move a lot, holding hands will not be very convenient. You don't want to hold hands for the first time when both of you are in a large group of friends or at a family gathering. The two of you don't necessarily have to be alone, but make sure it is a private place where both of you are comfortable. Try taking a walk on the beach, going for a hike, or taking a stroll down the street. You may have people around you, but strangers will most likely not pay attention to the two of you, giving you the privacy you need. A movie theater is a great place to initiate hand holding. Since you are sitting right next to each other, your positions are very conducive to holding hands. The darkness adds a layer of privacy and may help if your date is shy. Take their hand. When you've found the right time and place and you feel ready, walk close to your date and gently take their hand. Remember to be gentle and not to rush it. Make it as subtle as possible and remember to keep talking or walking to ensure it is natural and comfortable. Make sure you don't lurch forward and scare your date trying to take their hand. You don't want to give off the wrong impression at this early stage in your relationship. You can also try gently rubbing your hands down your date's arm before you link your hands. This gives them a heads up before you grab their hand and adds a nice, more intimate touch to your initial hand holding. If your date pulls away, don't force the issue. It may be that they aren't interested, but they may also just be shy and is not quite ready to hold hands. Don't take it personally and try to make them feel comfortable in the situation. You'll get there eventually. Start simple. Use the simple hand grasp technique at first. When you grab their hand, reach across their hand to where your palms are centered, making an X with your hands. Gently close your hand, wrapping your fingers and thumb around the edges of your date's hand. For the more intimate moment, consider gently rubbing your thumb across the back of their hand. This adds a layer of affection to your grasp and it lets them know you are enjoying the activity without you having to tell them. If they returns the gesture, you know you're doing it right. Try not to hold too tight. This can be uncomfortable and cause both of your hands to sweat. Make eye contact. If you want to get your date to hold your hand, start simple by making eye contact with them, smiling subtly. This lets them know you are interested in them and makes you seem open and receptive to physical contact. You can also try walking closer to them while you are walking. The physical proximity, added with the eye contact, will make you seem interested and responsive to their presence. Touch them first. Opening up the possibility of physical contact is important. Let your fingers brush at dinner or when you're walking from the car. If you are walking side by side, gently hold their arm or link your arms together. These are gentler forms of contact that let your date know that you are okay with touching. You can do a kind of hand holding test run by grabbing your date's hand and leading them somewhere, dropping it when you've reached your destination. This way, you hold hands for a short while but it isn't as nerve-racking as officially holding hands. Give subtle hints. Your date might need some clues that you want your hand held. Try giving them small hints that you want to hold hands. Your date might just be nervous, so encouraging them is always helpful. If you're in a theater, place your arm and hand on the armrest, palm facing up in invitation. You can also let your hand drop over to their side on the armrest. Your date should take notice and get the hint that you want it held. Claim your hands are cold. Tell them that your hands are cold or ask them to feel if they are. Hopefully, your date will see if they can help warm them up. This is a cute, flirtatious way to get your date to hold your hand. Ask if you can compare your hand sizes. Bring your hand up in the air and when your date raises theirs, gently place your palms together, comparing the sizes. This gets your date's hand close to yours and is a subtle way to let them know you want to hold their hand. Be bold. If for some reason your date has still not figured out that you want to hold hands, initiate contact yourself. Gently clasp their hand and squeeze it gently, letting him know you care. If you are nervous, it is likely that your date is as well. This may help both of you relax. Confidence and initiative are attractive qualities, so being the first to grab your date's hand lets them know that you are interested in them and that you want to become closer. Intensify the hold. Once you and your date have gotten comfortable holding hands, try taking the initiative this time and use a different, more intimate hand holding method. If you are clasping hands, open your fingers and move them until they are aligned with your date's fingers. Open your fingers slightly, pushing each of your fingers into the space between your date's fingers, interlocking your fingers. 
Gauge the level of interest. Check your hands. Wait for the right time and place. Take their hand. Start simple. Make eye contact. Touch them first. Give subtle hints. Be bold. Intensify the hold. 