There are two kinds of memorable first dates. This one, alas, was not the good kind.

My date was a well-educated, handsome man who was widowed about a year earlier. Exactly a year, in fact. We met for dinner on a Friday night and I, thinking I was making casual conversation, asked what his plans were for the weekend. He replied that his final grief counseling session was the next morning and that he planned to gather with friends and family on Sunday to mark the one-year anniversary of his wife’s death.

It was pretty tough to come up with small talk after that.

I vaguely recall mentioning that I was seeing my college sweetheart, who after more than twenty years still is one of my best friends. My date replied disapprovingly that after their marriage, he had not allowed his wife to maintain friendships with her ex-boyfriends.

Nope. No question about it. This evening would not go well.

War is hell
Everyone has first date war stories. Some are sad; a few are scary. Some evolve into amusing tales. But there’s nothing funny about them while they’re in progress and your only thought is: "How did I get into this, and how do I get out?"

Possibly the most common deal-breaker on first dates is The Lie. You discover with dismay that your date bears no resemblance to what turns out to be a 10-year-old photo — back when he had more hair or she had fewer chins. I’ve lost count of the number of times a man who claimed to be my height (north of 5'9") proved a couple of inches shorter — and then got angry with me because I had lied about my height!

Shallow concerns about appearance aside, it’s no fun when your first impression of your date is that he or she was dishonest with you.

A timely investment
Most of the time, of course, first dates that disappoint do so for less dramatic reasons. We’ve all been on both ends of that elusive "lack of chemistry" thing. While generally I hold to the three-date rule — which allows for the possibility that first-date jitters prevented you from seeing your date in the best light — there’s no point to prolonging everyone’s agony if you’re absolutely sure it’s not going to work.

In that case, you owe your date an honest but diplomatic goodbye. They’re not fun to deliver or to receive, but when you compare them with weeks of unreturned phone calls and postponements of the inevitable, they’re a lot better than the alternative — and they allow everyone to move on to a happier, more long-term match!

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