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Holding hands should be something that is enjoyable and brings two people closer. Holding hands for the first time is a special moment because it means you are putting yourself out there. Even if you've been thinking about it for a long time, if you decide to ask her to hold hands, it shouldn't be the first thing that comes out of your mouth when you see her. This may come across as abrupt as opposed to romantic. Make sure you are somewhere where you and your girlfriend feel comfortable. Try not to be somewhere that is too loud or distracting. For instance, try not to be in a really loud restaurant with TV's blaring from every side. This is probably not the place that your girlfriend wants to have this special moment with you. You also probably don't want to hold her hand for the first time in math class, or somewhere that both of you would rather not be.This moment should be about your relationship, not anything else. Take it off your mind for a while when you first see her. Settle into how you usually are with each other and make sure that you're not thinking about it too much. If you think too much about when you are going to take her hand, you might come across as quiet, worried or even bored.  Instead of thinking "Should I do it now? Or maybe I should do it now?", try to relax. Make her laugh. This will make the moment even more special when it happens. If you are nervous and can't stop worrying about when you are going to ask her, take it off the table. Think to yourself, "I don't have to ask her today. I can always ask her some other time". Giving yourself the option to postpone takes off the pressure and will help you relax. You may even find that it will relax you enough to actually go through with it! You can tell an amazing amount about what a girl is feeling or thinking by reading her body language. You could even argue that body language is more important that what someone actually says, because it shows their level of comfort and interest. This is why if you are ready to take her hand, you should test the waters first and try to pick up cues about whether she wants to hold hands. Some examples of positive and receptive body language include:  Smiling Leaning towards you as opposed to away from you Having her face, torso and feet pointed at you Mirroring your gestures or expressions Seeming relaxed as opposed to stiff Does she seem to mind you getting closer? If she moves a little bit away as you move closer, she may not yet feel comfortable holding hands. However, you can tell that she is interested if she does not move away and if her torso and feet are pointed towards you as opposed to pointed away. If someone has their body pointed towards you while you are close together, it shows a level of comfort and trust. In the course of conversation, see how your girlfriend reacts to your touch. If she says something funny, touch her shoulder and tell her how funny she is.  If she is receptive to you getting close to her and doesn't try to create distance between both of you, then you'll know that it's a good time to ask her.
Don't immediately go for her hand. Be somewhere special. Get comfortable with her. Read her body language. Get a bit closer to her. Test out physical contact.