What to Say

First, relax. Try not to view it as a date, look at asking her out as an invitation instead. Better still — take the pressure off by not using the “D” word altogether. Don't ask for a date and don't call it a date. It starts to get significant when that word appears, so focus on the activity and position it in the same informal way you would ask a friend.

Keep the invitation light and casual. A lunch date is low pressure — it has a beginning and an end, and both occur within an hour or so. It's easy to say goodbye, there's no goodnight kiss, no obligation, and so the pressure is off.

Here's What Not to Say

• Don't ask, “You want to go out sometime?” It's too open-ended and can lead to an awkward follow-
up conversation.

• Don't ask, “What are you doing Friday night?” It's too vague and it might leave your potential date wondering if you're just curious about what he or she is doing on Friday night, or if you want to do something together.

• Don't use a sexually suggestive line like, “I'd love to have breakfast with you. Should I call you or nudge you?” It might be funny if you read it in a book, but in the real world, it's liable to get you a speedy rejection.

These types of lines don't show that you're genuinely interested in a person — they make you seem a little too slick.

What Works Best?

Before you ask, consider the following:

• Be a friend first, not a potential date. If you really want to get to know someone better, the key is to relax and allow your own personality to shine through. There really is no need to be a smart-ass, or make them laugh out loud. You just need to be good company, because the more comfortable you both feel, the easier it is to recognize any chemistry between you. In short, forget the pickup lines. Show an interest in them, and they will only be flattered.

• Create an opportunity for your date. Once you know more about what that person likes to do, you can offer something. After all, a date is an invitation. If they love art, ask them to the latest big museum exhibition; if they like sports, offer tickets to a basketball game. If they enjoy wine, ask them to a wine tasting.

• Drop a hint. Ask about a subject and drop a hint. Say something like, “What do you like to do on the weekends?” As she responds, look for something you like to do too. If she says she loves to hike, respond with, “We should go hiking together sometime,” then move on in the conversation and ask about her favorite hiking spots. You've just dropped a big hint, so let it sink in for a while. Listen carefully to her response and gauge her enthusiasm. If she stays upbeat and positive, ask her if she would like to go hiking with you next weekend.

• Keep it casual. If you feel uncomfortable saying, “Would you like to go to dinner Friday night?” try something like this:

“I was thinking about going for a ride along the boardwalk on Sunday. It's going to be a beautiful day. Would you like to go with me?” Pose the question as if you're already going and they can join you, if interested. This will make you feel less desperate and take the pressure off them if they say no.

• Be specific when asking for the date. “I'd like to take you for coffee this Thursday” is more powerful than asking if she'd like to “go out sometime.” Of course, you could always invite the person on a group date, since that really takes the pressure off.

Invite them bowling, to play volleyball, or to join a bunch of friends for a drink or to a party. As soon as you say, “A bunch of us are going to…” it takes the pressure off. “Us” is the operative word here.

Read the situation. If you've hung out for a while and all the signs suggest your potential date shares your feelings, then either a) you won't be able to keep your hands off each other, or b) you'll be able to suggest meeting up for an evening out knowing that's what they want too! If that vibe isn't happening, at the very least you'll have made a new friend.

So remember, when you are asking someone out, plan ahead and be specific. Know what you are going to say AND what you want to suggest doing on the date. Your prospective dates will be much more comfortable if they know exactly what you want to do. Just try to relax and enjoy yourself. Worst case scenario— they'll say they can't go out. And that will bring you one step closer to someone who can. Someone who appreciates you and where the chemistry connection is reciprocated and the sparks really fly. Let's face it, getting to that special someone inevitably means dealing with a few duds along the way. It'll be worth it in the end.