The Dating Game: The First Date

How to Pop the Question. No, not that one! We haven’t gotten there yet! I’m talking about asking her out for the first time.

When to Ask. If you meet at a party/bar/church (i.e., in person), unless you’re getting a really good vibe, ask for her number but don’t ask her out. If she gives you her number, even a work number, that’s a good sign. If she won’t give you her number, well, aren’t you relieved that you didn’t ask her out and get rejected in front of all those people at the party?

Let’s assume you did get her number. Call her! Not that night, though! But don’t wait too long. A week is too long. She could be dating someone else by then. She could forget who you are. Calling two days later is good. Shows that you’re not desperate and that you aren’t trying too hard not to look desperate (calling her the same night does look desperate and/or weird). But don’t be anal about how long you “should” wait to call her; the next day is fine, three days later is fine.

What to Say. If you’re asking her out on the phone and you’re nervous about it, write out a script in natural conversational language. You don’t want to *sound* like you’re reading from a script! Destroy all evidence of the script afterwards and no one need ever know… Here’s an example:

“Hi. Is [Kate] there?”

This is she.

“This is [John Smith]. We met on Saturday at [Marty’s party].”

Oh, hi!

“How are you?”

Great! How are you?

Ask a follow-up question to something she said directly to you at the party--e.g., how was [blockbuster movie that she said she was going to see]? Caution: if she did not mention this activity directly to you, do *not* mention it. It’s a little creepy that you were listening *that* closely.

Chit-chat about the movie.

“I had a really good time meeting you and was wondering if you wanted to go out for [coffee, a beer or something equally casual and plan-less].” Suggesting something like paddle boating at the lake is too thought-out and fake-y date sounding. Equally bad is suggesting a movie, the theatre, a symphony, etc. How weird is it to sit in the dark next to a stranger you’re with but can’t talk to? Doing something casual in the afternoon still leaves you the option of extending the date into dinner if things go well.

I’d like that.

“I was thinking we could meet up at [coffee shop, bar]. Do you know where that is?” [Always default to meeting the woman at the location of the get-together (not at her house or yours) for at least the first date, even if not the second and third. It’s a safety thing for women. And it allows both of you the freedom to leave at any time and have the date be done if it hasn’t gone well.]

That sounds good.

“Does next Saturday work for you?” [Hopefully she’ll suggest a time.]

Yeah. Around 2 would work best for me.

“That’s good for me too. Well, I’ll let you go, but I’ll see you on Saturday!”

You could start a real conversation with her and not hang up so soon, and do stay open to that if she initiates, but I would advise against it. I've written a bit about this before, and here’s why I'd generally not get into a long phone conversation. One, she may be busy, so you don’t want to monopolize her time. You can ask “Is this a good time to talk?’ (which is often a good idea even for a short phone call), but isn’t that what the date is for, so you can talk more at length? Thing is, most people are awkward on the phone, even normal people, much less you. Starting a conversation out of the blue is difficult enough in person when you have visual cues to scan for to tell you how bored/interested she is in a particular topic. And when you meet in person you have something in common to talk about (the weather, the location, how good the coffee is, how busy the place is, etc.). Not that you want to dwell on those superficial conversation topics for more than a minute or two, but they provide a jumping-off point. So, in the beginning, stick to using the phone as a tool to set up a time to talk to her unless you feel comfortable with phone conversation.

If you met online, it’s pretty easy to ask her out. Just send a normal email like you’ve been sending her and append to it one line: “Do you want to meet up for coffee this Saturday?” If she doesn’t respond to your query, she’s not into you. There is no reason a woman would not respond in some way to your question. She wouldn’t “forget” that you asked. And if she’s just not ready yet to meet, she’ll say so.

Up on Tuesday: What to wear on a first date and first date etiquette.