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Know if he is not ready. If you are out to dinner, and he is across from you, you can reach for his hand over or under the table. If he pulls away, stop, he is not ready! You never want to push your partner into doing something they don't want to do. If you pressure him, he may feel awkward and break up with you. If you are sitting next to each other, you can easily hold his hand, without stretching your arms out. If you are watching a movie, or a play, he may put his arm around you. If so you can reach your arm out and rub his hand (the one on your shoulder, or his free one). He may bring his hand up, and you can lock fingers. If he does pull away or seems uncomfortable with holding hands, STOP, and whatever you do, don't seem offended. If you do, he may feel like you are mad at him because of his opinion and that is not a good situation. You may apologize, or just slightly nod, and show you understand.
Put your hand near theirs. This works well if you are sitting or walking next to each other, but make sure their hand is at their side. Hold your hand very close to theirs, even maybe touching a bit, but look straight ahead. Don't freak out or stare down at your hands.
Move your hand even closer, and soon, very slowly put your hand in theirs. Try brushing your hand against theirs. Say that you want to compare your skin tones. This is a great way to get closer to holding their hand. Close it around their hand. This would be a good time to look up at them. If they just stare at you, smile. If they pull away, just quit all together. They are just not ready to do this yet. Holding their hands and looking into their eyes can create a nice tension, which is perfect for a first kiss.
Watch for signals. If your significant other seems to be enjoying themself, holding hands with you, this is good. They are comfortable with this, and if you think you are ready, intertwine your fingers in theirs. They will eat this up! If your partner doesn't seem interested in holding hands, it doesn't hurt to ask what's the matter. It's possible that they're simply nervous or sweating too much.
Proceed at the right pace! You are holding hands with your cutie! Yay! If they don't like it, don't worry! They are nervous and just not ready! If they pull away, do not try to hold hands with them again that day!
Move on to hugs, more touching, and maybe a little kissing! This is a slower process. Do not move into this too fast. If you do, they will think that you are a creep and will make fun of you behind your back.
Be understanding! It's okay if they either jerk away, or look down. Everyone has their own speed. If you freak out they will understand. But just keep trying different days until they are ready. If you don't feel comfortable, you are okay! Holding hands isn't the most important thing to do in a relationship.
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