The first piece of dating advice is to talk to the guy or girl before the date and agree upon what you’re going to do and who will be paying for it. Otherwise, you risk those awkward moments of coming to the door in a killer cocktail dress ready to dine at the best restaurant in town while he shows up wearing shorts and a Burger King t-shirt. It’s also discomfiting when the server sets the check down and it just hangs there in the middle of the table. Therefore, avoid these minor embarrassments by planning it all out. The second piece of dating advice is to plan an activity that does not require constant interaction. It’s hard enough to find five hours’ worth of conversation when you’re with someone you know; with a stranger, it’s excruciating. So go to a movie, play, or sporting event, or take a sightseeing tour. (Ghost tours are great—they give you a perfect excuse to hide your face in your date’s arm.) Later, when you’re grasping for conversation subjects, you’ll be able to recap what you did during the first part of the date.
Let’s be honest, some dates are so bad that they are unsalvageable. Is there any dating advice about cutting them short? Fortunately, yes, you have a couple of options. First, you can pre-arrange for a friend to call you halfway through a first date. If the evening’s going well, tell your friend you’re having a great time and hang up. If it isn’t, feign a look of concern and say, “Oh, my God, which hospital? I’ll be right there!” Exit stage right. The second option is probably the best: honesty. Unless you’re dating someone with the sensitivity of a stone, your date is probably just as aware as you are that things aren’t clicking. And like you, there are things he’d probably rather be doing. Be the gutsy one to take the bull by the horns and say, “Look, Dennis, you’re a nice guy, but I’m just not feeling any chemistry here, and you don’t seem to be, either. Let’s call it a night.”