You can also try gently rubbing your hands down your date's arm before you link your hands. For the more intimate moment, consider gently rubbing your thumb across the back of his hand. You can do a kind of hand holding test run by grabbing your date's hand and leading him somewhere, dropping it when you've reached your destination. If you're in a theater, place your arm and hand on the armrest, palm facing up in invitation. Relationship coach and author of Get The Guy Matthew Hussey has analysed thousands of dates and men in his quest for the perfect relationship.
If you're out on a date, look for subtle signs that he might be ready for you to hold his hand. 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.[2] 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.
Since you are sitting right next to each other, your positions are very conducive to holding hands. You might be a little nervous, so check your hands to make sure they are not sweaty or clammy. When you've found the right time and place and you feel ready, walk close to your date and gently take his hand.

It may be that he isn't interested, but he may also just be shy and is not quite ready to hold hands.
This adds a layer of affection to your grasp and it lets him know you are enjoying the activity without you having to tell him. If you want to get your date to hold your hand, start simple by making eye contact with him, smiling subtly. Bring your hand up in the air and when your date raises theirs, gently place your palms together, comparing the sizes. If for some reason your date has still not figured out that you want to hold hands, initiate contact yourself. 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.
Either way, there are some easy steps you can follow in order to get to this crucial and romantic first step. If your date has been giving you the cold shoulder all night, this is a sure sign that he is not interested. If they are, subtly wipe them off or stick them in your pockets for a moment to dry them off. When you grab his hand, reach across his hand to where your palms are centered, making an X with your hands.

If you are clasping hands, open your fingers and move them until they are aligned with your date's fingers. But if he has been walking close to you and seems comfortable, this is a good signal for initiating hand holding. Gently close your hand, wrapping your fingers and thumb around the edges of your date's hand. These are gentler forms of contact that let your date know that you are okay with touching. Also telling a guy too soon that you are falling for him is unnecessary and a little scary. He'll feel your attraction by watching how you are around him, you don't need to verbalise it too soon.

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