How to Sneak Your Arm Around Your Date

Preparations

Be sure it's time to get this intimate. While putting your arm around your date isn’t an overly invasive gesture, it usually signals that you're interested in a romantic, more deeply connected relationship. Before sneaking your arm around, be totally sure that you're ready to send out these signals! If it's your first date, it might move things too quickly, especially if you're serious about getting to know one another properly. And if you feel that you don't have romantic feelings toward your date after all, but would like to stay in the "friend zone", avoid the arm sneak altogether, as it'll send out the wrong signals and isn't fair to your date.

Check for signs of your date being at ease. Are you getting signals that your date wants to hold hands or get cozy? If you can read your date, you may see your date's own strong signals that he or she wouldn’t mind you getting closer for an intimate snuggle. This can help you pluck up the courage needed!

Choose the right time and place. There are wrong times (such as when he's slurping his linguine with clam sauce or she's trying on a pair of shoes) and there are right times to sneak your arm around your date. Choose an intimate moment and exercise patience––the right time will present itself in due course. Perfect arm-sneaking times include: At the movies during a romantic, sad or scary point in the film. This classic arm-sneaking territory is so well used precisely because it contains all the necessary elements––darkness, close proximity, potential need for comfort during a scary or hairy moment in a film, comfortableness of the seating, and general inability to look at each other, something that could otherwise break the arm hold spell. Just be careful not to send out the wrong signal (such as sneaking an arm around during an explicit sex scene) or spoiling the climax of an action scene with a distracting arm sneak. Emotional scenes or scary scenes are usually good bets. Walking down the street. If you're walking closely together and talking, this can serve as an ideal moment to sneak an arm around your date. Time it to coincide with a meaningful or caring discussion; avoid any moment that's too mundane or involves a heated discussion about politics. A good moment is when you're both expressing awe at the beauty of the day or the prettiness of the flowers along the path. When seated together at drinks or a party. Depending on where you're sitting, a dirty martini or a plate of tapas might just present the ideal moment for sliding your arm around your honey. Another opportunity might be during special announcements or when making a toast––after speaking, slide your arm behind your date's back or shoulders in a friendly gesture of celebration.

Make sure you're both close enough so that you don’t have to reach. Arm sneaking isn't about struggling, strangling or finding yourself dangling! Make sure you're in a comfortable spot and close enough to your partner. Avoid any arm sneaking if there's a risk you might become unbalanced and end up using your date as support! The best position is to be side by side, so aim for some shoulder to shoulder closeness.

If you're shy or sly, combine the arm sneak with another movement, so that it all appears seamless. For example, offer your jacket to your date if it's cold and then simply leave your arm there after placing the jacket on. Or talk and move at the same time, such as saying "You know that I find you so adorable", while sliding your arm around his or her back at the same time. Or go window shopping together and as your date is peering at something closely, sidle up and mention how interesting the items in the window appear, while at the same time sneaking your arm around your date's back.

Make it fun. Try this on for size: Ask your date "If you were a pirate, would you have a parrot on this shoulder (point to the shoulder closest to you), or this shoulder (point the shoulder furthest from you)?" When your hand reaches the shoulder furthest from you, casually just leave your hand there, with the arm draped around your date's back. Done! This can get even more intimate… Try asking: "If you were Casanova, would you kiss someone on this cheek, or on this cheek…" You get the drift!

Have courage but don't go over the top. If you're certain that it's the right time and place, then go with your instinct and trust that your date is ready for the arm sneak. On the other hand, if your date shrinks back, asks that you kindly remove your arm or looks horrified, then it's either too soon or it's never going to happen. Be polite and remove your arm with a short apology and simply move on by suggesting that the two of you do something else. The implications of the response may be something you need to reflect on, and you may even need to discuss the future of your relationship after some reflection.

The classic yawn and drop arm maneuver

Choose the right place. This move can be made at the movies, in a bar, wherever you're seated together, etc.

Wait for your date to appear at ease. This includes signs of having settled in comfortably, not talking too much (nerves) and enjoying the occasion.

Start yawning. Bring your hand up to your mouth to "stifle" the yawn.

Follow the covered yawn action with a stretch. Raise the arm closest to your date into the air behind you as part of the fake stretching post-yawn. Leave it there for at least 5 seconds to convince your date you are really yawning.

When bringing your arm back down, oops, it appears to have rested on the shoulders of your date rather than returning to your side. Done.