<Valentine’s day humor / cynicism>
I think that today is the best day to start a relationship. Of all the days in the year, if you had a choice (which you never do), I’d recommend you start today.
First, by starting dating today, you’ve missed the "holiday gauntlet," which starts with Halloween and continues through, well today. Basically, from October to February, there’s 1 holiday per month that has heightened expectations from your partner. Halloween? Better be with your partner. Thanksgiving? Christmas? New Year’s? Valentine’s Day? All of these come with added pressure from your mate. After today, the next holiday with any special ‘couple’ significance is July 4th. Sure, we have Memorial Day in May, but traditionally that weekend is full of social exercises that you’d do anyway – like hiking, camping, or enjoying something like the Folklife Festival. Your mate isn’t going to flip if you don’t do something "special" over Memorial Day. So essentially, by starting dating today, you have the most time available to you to get to know your partner without a holiday interfering.
Second, if you do actually start dating someone today, your anniversary is very easy to remember and doubles as Valentine’s Day, meaning that’s one less day a year you have to do anything special, buy gifts, etc.
Finally, by starting on Valentine’s Day, you don’t actually have to do anything magical or special for Valentine’s Day itself that year. No woman or man is going to say, "our first date was on Valentine’s Day and I didn’t get chocolates or flowers. Damn them." No one expects those things on a first date anyway. All you have to do is go out on a regular date, and in some ways the pressure is off because everyone knows it’s Valentine’s Day and your first date will be by necessity very un-Valentine’s like.
Now, don’t get me wrong – I’m not saying that you (or I) can’t start dating on any day of the year. I’m merely pointing out that, if you’re going to start, today is the best day of the year to do it.
Happy Valentine’s Day!