The success of humor, like many interpersonal behaviors, may depend in part on contextual factors and individuals' goals, so the savvy comedian will need to read these carefully before offering a quick-witted comment. In general, err on the side of positive humor (DiDonato et al., 2013), such as spontaneous, warm humor that builds off of shared experiences, the surroundings, or everyday news or events. For example, if a cute passerby spills a drink, resist the urge to sarcastically poke fun (e.g., "Remind me never to wear nice clothes around you") and instead, relax, smile, and create a connection (e.g., "I agree – this floor needs a good cleaning"). The good news is that failed humor may still leave the door open for a short-term affair, but keep in mind that prospective long-term partners are discerning, using whatever clues they can to navigate the uncertain process of finding a good partner.
As a final recommendation, if humorous remarks are not your forte, you might be wise to pursue an alternative flirting strategy, at least initially. Better to think long-term and allow your other strengths to shine than to offer a line that is canned or, worse, not actually funny. One explanation for why humor sometimes fails as a relationship starter is that sometimes an intended humorous comment leaves no one laughing (Bale et al., 2006; Weber et al., 2010). Even if the right kind of humor can be a quick, effective, and pleasurable strategy for conveying a wealth of positive mate characteristics, direct approaches or compliments are preferable to weak humor (Senko & Fyffe, 2010). Remember too that people will find you funnier if they are already attracted to you (Li et al., 2009), an important detail to keep in mind as you think about how humor can best fit into your toolbox of flirting tactics.
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