This post is for everyone who actively dates, but I'd like to direct it mostly at middle-aged men (my dating pool). If you're on a first date and you're talking and your date's eyes start to glaze over, switch to asking your date questions and get her/him to talk more. Don't keep trying to fascinate the other person with more talking, certain you'll eventually hit upon the funny story or riveting information that will make your companion want a second date. If your date doesn't seem engaged by whatever you're saying, please switch to asking questions and listen for a while. Ask "What do you think?" Ask "Has anything like that ever happened to you?" Ask "Did you use a crosswalk today?" Ask anything.
I think people (men) must go into a "like me, please, like me" mode, hoping you'll get a good response if you just keep talking. But the truth is that we'll often like you better if you act interested in us, and you do that by asking questions. Not asking questions makes it look like you're not interested in us and that lowers the likelihood that we'll like you. Questions that get us talking are much better than story after story about your job (or your kids). Thanks!