Pickup Tricks

Is there a cool way for a guy (or a woman) to ask out a complete stranger?

My friend was recently followed on the street in Center City by a random guy looking to pick her up. He even tracked her into a Victoria’s Secret to say “hello.” The whole idea creeps me out, so I thought I’d ask: Is there any cool way for a guy to ask a woman who’s a complete stranger out on a date? If not, and just in case he’s reading, can you please give this dude some advice? — J.W., Center City

In short, yes, there are many cool ways for a guy to ask a complete stranger out on a date. Stalking someone and following them into a Victoria’s Secret is NOT one of them. It’s an art and science to execute this mission without being creepy. But it can be done, here’s how: [SIGNUP]

First, It takes a TON of confidence to take that initial leap of faith and break the ice. While the thought may seem scary and intimidating, go into it with the mindset of “What do I have to lose?!” Nothing! The fear and intimidation we feel is because no one wants to be rejected. This should not be enough to dissuade you from not trying! Even if you don’t get the response you were hoping for, you will feel proud of yourself for making the effort and overcoming your fear of making that first move.

If your eye catches someone who stops you in your tracks, here’s your chance to practice being proactive in your love life. Tell her you noticed her and add an authentic flattering comment, perhaps about her knockout shoes. Everyone appreciates a genuine compliment. Regardless if she is interested, she should be flattered. It is okay to mention that you usually do not approach strangers like this, but you just couldn’t help but come over and say hi.

Then, let it flow naturally. Introduce yourself and strike up a light and breezy conversation. Be sure to pick up on her cues to see if she is happy you approached her. If you are short on time, get to the point. Let her know this is abnormal for you but there is something special about her. Ask if she is a free agent and perhaps interested in getting together. If so, give her a business card so she feels comfortable. Tell her that you’d love to hear from her so you can take her out. This way she can take the initiative and you are not stalking. Then exit right. Don’t overstay the chat, so you are respectful of her time and space. You’ll look like a class act that also has places to go and people to see.

Keep in mind that you already have kudos points for getting the courage to break the ice. If you can maintain a laid back, friendly composure I would be surprised if she didn’t call or e-mail you pronto.

Finally, while this scenario applies for guys approaching women, ladies, you are just as capable of doing the same! One thing I always say to single women is that it no longer pays to be old fashioned. If you see someone who catches your eye, go up to him. Women are just as capable of controlling their destinies and romantic endeavors as men are. The whole experience can be quite thrilling as long as you take each step of the introduction slowly and employ friendly, socially prudent, conscious judgment. The rewards will far outweigh the apprehension and fear you initially felt. Even if you get turned down, you will feel proud of yourself for taking the leap and giving it a go. Never let fear dictate your course of action or prevent you from meeting someone who could potentially be great for you!

Finally, never EVER ask someone out while they are buying or doing something personal. As a general rule of thumb, guys, you should never step foot in a Victoria’s Secret unless you are there to pick up a gift for your girl and in that case, you shouldn’t be interested in how to approach a stranger.

Monica Mandell, Ph.D. is the Director of the Philadelphia office of Selective Search, the premiere (off-line) upscale matchmaking firm for the most eligible singles. Please send your questions to: monica@selectivesearch-inc.com