Before we get to this week's question, there's a little housekeeping to take care of. First of all, thanks for all the positive feedback I've been getting about the column so far! I'd love for more of those comments to go directly on this site (as opposed to on Facebook or in my personal inbox) so that perhaps we can get some conversation going. Also, I've gotten feedback that it's hard to know when there's going to be a new post. Two solutions: 1) the answer is every Monday and Thursday, and 2) sign up to follow the blog, and you'll get an email every time there's a new post. Finally, keep the questions coming!
If the first date wasn't that great, when is it still worth giving a second date a shot?
Second time around
Without knowing any of the particulars, I'd say it's almost always worth giving someone a second chance. Nerves can get the best of anyone on a first date, and sometimes it takes more than one meeting for two people to click. If there's any possibility that you might wonder if he or she could be the one that got away if you opt out of the second date, spare yourself that worry, even if it means you're gambling on having a sub par night.
Now here come the caveats.
If your date does something egregious on the first date, you don't need to feel pressure to waste your time. However, think carefully about how you define egregious. If I've learned anything from all my conversations about dating, it's that one person's deal breaker is another one's turn-on, and also that characteristics that are indefensible in one person might be attractive when displayed by someone else. OK, that's two things, and here's a third: Some people's lists of deal breakers are so long that there's unlikely to be any human on earth who fits the bill.
If you find yourself leaning toward going on a second date either because you can't figure out how to let the other person down gently or because you feel sorry for him or her, forget about wasting your own time — you're unfairly wasting the other person's time (and possibly money) and sending a false message about your intentions. If this is the situation, politely say (email is fine if you've just met), "It was nice meeting you, but I'm not interested in taking this any further." Don't add "right now" or any other qualifiers, which will just confuse the situation.
As long as we're on the subject of first and second dates, I've heard of a recent trend of people going out to dinner on a Saturday night for a first date. This is a bad idea, and even though you didn't ask, I'm advising against it. The exception is if it's someone you already know, and you are absolutely positive that you will have an amazing time. There are too many expectations about Saturday night dates, and dinner is too much of a financial and time commitment to invest in someone you don't know. Whether it's a first date with someone you met online who you haven't yet met in person or some other blind-ish date scenario, pick a weeknight, get a drink or coffee, call it a night, and hope it goes well enough that there's no question about whether or not there should be a second date.