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Regular readers will know that yours portly is back on the prowl, a lonely hunter stalking the forgotten byways of twenty-first-century romance like a sleek panther ready to pounce upon an unsuspecting gazelle.

This time around I’m very much taking the approach that dating should be fun, and not something to be rushed.  Despite some of my anti-femite proclamations, I very much enjoy the company of women.  Yes, some of them are insufferable, and their blather about inconsequential trivialities—and their refusal to take proactive steps to improve their lives and situations—is mind-numbing.  But having a good meal with an attractive and interesting woman is a pastime I relish.  My general thought process these days is that, even if nothing comes of a date, it will at least have been a couple of hours of interesting conversation and delicious food.

That attitude has been somewhat liberating.  Yes, I’d love to meet a good woman to wife up, but if that doesn’t happen, no big deal.  With that outcome-independence—not investing emotionally or otherwise in the outcome of any given date or interaction—I have newfound confidence.

With that confidence I’ve been engaging in a challenging but very rewarding bout of cold approaching.

“Cold approaching” is striking up a conversation with a stranger—in this case, women—and, in a short span of light conversation, obtaining her phone number.  Initiating a conversation with a random person is a test of one’s ability to be interesting and sociable in what might otherwise be an awkward situation.

I’m not claiming to be great at it.  I’m not promising crazy outcomes if you just “follow these five steps.”  I’ve only cold approached (recently) twice.  I’ve done it maybe once in the past.  I don’t count using a dating app at all, even though I could hear some wag arguing, “But, portly, aren’t you also just approaching someone cold?”  No, because that person can at least look at some pictures of you and see your responses to some goofy prompts.

Anyway, I’m two-for-two in terms of simply getting the number.  That’s actually the easy part.  So far, I have not converted those into dates.  One of them I am certain will not move in that direction—at least not in the near future.  The other I am uncertain about; it remains to be seen at the time of writing.

Here is basically what I did in both scenarios:

1. Noticed the girl I was interesting in chatting with
2. Opened a conversation complimenting some unique element of her outfit (in both cases, their dresses)
3. Made a quick introduction of myself (after a brief exchange of pleasantries; see #2)
4. Asked if she’d like to grab coffee or get dinner sometime
5. Secured the number (or, in the case of the first girl, gave her my number—an initial mistake on my part) and hit the road!

The key in both cases was just doing the thing, and realizing that the outcome did not matter.  When I cold approach again—which I likely will—I will have that same mentality.  You can’t care what the answer is (although, obviously, I’d like them to be receptive).

For the curious, I’m going to break down both interactions in a bit more detail.  I don’t remember much, mainly because I was just “flowing” with the conversation, but I’ll relate what I can recall.

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