Online Dating: Get the Real Date

by Michael on November 18, 2010 · 0 comments

If you get to this point, you've graduated the course.

Update: The Tao of Bachelorhood Guide to Online Dating, based on this series but revised for the Kindle, is available on Other versions to come. For a limited time it’s only $1.99!

Concluding our series of online dating tips, let’s look at the endgame: what happens after you make online contact. Let’s face it, the process of putting up your profile, finding like-minded-yet-attractive women and crafting a great first-contact message are all just the lead-up to securing that real-life meeting.

Once she responds favorably to your contact, your goal should be to move quickly to that first face-to-face meeting. After all, while email flirtation can make for a nice fantasy, it doesn’t tell you how you’ll like her in person. While your communications with her will be shaped somewhat by her questions and both your schedules, there are some rules to live by:

  • Remember the rules of your first contact. Be playful, keep a little mystery, ask questions. Some women will practically write you a novel; don’t write her a novel back (unless you’re both writers and the wordplay is awesome). Similarly, if she’s a little terse, try and playfully draw her out. But if it looks like you’re just not meshing, thank her for her time and move on.
  • After the third e-mail message, you should be either talking on the phone or meeting in person. There’s a disorder I’ll call “Forever Online Syndrome.” Its symptoms include the continued refrain, “I just feel more comfortable staying in email for a while.” If she’s not there to meet actual men in actual meeting places, you should terminate and focus your energy elsewhere. (No, I don’t care how hot she looks in her photos. She may be stalling because she’s now 50 pounds heavier.)
  • Offer her your phone number. She should have a plan for making contact with men—if she can’t call from a blocked number, Skype is cheap and Google Voice is free, and both can be changed or deleted easily if she feels threatened. If she’s scared to talk on the phone, it’s a red flag.
  • If she gives you her number, call, don’t text. There’s a time and a place for texting, and it’s not now. You want her to feel comfortable hearing your voice, and you want to hear hers.
  • Set up your meeting during the phone call. In the rare instance where she would rather move straight from email to in-person meeting, that’s fine, but just like e-mail you should avoid multiple phone calls. If she isn’t comfortable meeting you after you call her, you probably want to move on.
  • Offer a choice of meeting times. I will usually give her three different days I can meet. It’s a good idea to avoid Friday and Saturday nights, but weekend afternoons are always good.
  • Meet in a busy public place. Yes, it’s a cliche, but coffee shops are probably the best initial meeting spot. They take alcohol out of the equation (although you can always move to a bar or restaurant if things go well) and enable a quick exit if the reality doesn’t match up with the online fantasy. Another option might be a popular museum, a busy park or even a sporting event.
  • If you like her, flirt! This is where you start using your real-world skills to get to the second date or beyond. Your advantage: you have information about her. However, the rules are the same. Be a good date, and recognize the signs that she may or may not be interested in the “real” you. Here’s some great advice for the first date.
  • Have options to move to a full-fledged date. My go-to spot for meeting women I met online was a coffee shop on the local beach, with access not just to the seawall, but several nearby bars and restaurants. From coffee, we could move to dinner, then to a walk by the beach. That’s like three dates! If there isn’t a beach in your town, you may have a riverwalk or a downtown entertainment area.
  • Don’t let her force sex on you. Oh, you laugh! There are a few women on every dating site who really want a little fast action, or an affair, or just all of a sudden believe they really like you. I’ve experienced this first-hand (think candles, wine and soft music…and I was only stopping by to pick her up!) I’m not gonna tell you not to sleep with her, but at least be safe, okay?
  • Even if it isn’t “on,” be polite. Once you realize that one or both of you just isn’t into it, move smoothly to end the meeting. Thank her for coming, and give her the same respect you would if you did like her (or she you). If she’s parked far away, offer to walk her to her car—but don’t be pushy about it. If she turns down the offer, let it be. And resist the idea that you need “closure.” If she isn’t interested, that’s her problem, and you should move on.
  • If she’s not in the same town… Dealing with a woman who lives a distance away is a special set of circumstances. I’ve done this myself, sometimes with success, sometimes not. I’ll give you one rule of thumb: if one of you isn’t prepared to travel to meet the other fairly soon, let it go. It might seem cool to have an “Internet girlfriend” for a while, but eventually one of you is going to get antsy. The closer you live, the sooner you should meet, but no matter how far apart you are, there should be a plan. I’ll look at this more in depth soon.

Basically, meet soon, then treat her just like any other girl you meet in real life. Just do me a favor and when you start dating in earnest, take down your profile, okay?

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