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How to survive a boring date — and even enjoy it


There are all kinds of bad dates. Meetups where the other person is late, rude, just not a match — or all of the above. The boring date is a special kind of awful. When you have absolutely nothing to talk about, or your go-to stories or questions lead to conversational dead-ends, sometimes you cannot help but think: Is it me? Am I the boring one?

You might be. In which case, you might stop reading now.

If you are fairly certain you are in fact fascinating and just happen to be sharing coffee, a cocktail or a meal with the equivalent of human anesthesia, here are some tips from my readers, colleagues and my own dating life on how to survive a boring date — and maybe even enjoy it.

It is not your responsibility to fill every silence. See what your date does with one or two of them. Are they boring, or just shy? It can be hard to tell at first. Especially if, like me, you are an extrovert who can easily fill any conversational lulls with more questions or stories. Because my tendency is often to fill any gaps in conversation, occasionally I like to let silences linger for a minute and see what my date does with them. Do they ask a reciprocal question, tell a story or launch us down a rabbit hole about whether it is better to die in a fire or a mudslide? Or maybe they do absolutely nothing. In which case, you might decide to go into interview mode.

Do a deep-dive on your date’s obsessions. Even if you are not interested in the person in front of you, they likely have at least one interesting thing about them. When “tell me about yourself” gets you nowhere, “tell me about how you got into civil-war reenactment?” or “why are you still hunting Pokémon?” might do the trick. Just about everyone has something they are passionate about, or a big challenge they have overcome. Generally people like to talk about themselves.

Play a game with yourself. When I was on a date with a man who just could not maintain eye contact, I coped by tapping my foot under the bar, marking the seconds that elapsed between him staring off into space and then occasionally looking back in my direction. I knew something was off with the interaction and rather than dwell on it, I at least kept myself entertained.

Shelbie Bostedt, a recent Date Lab participant, tells me when she is bored on a date, she sees how often she can slip an odd word like “banana” into conversation. “I’ve tried to slip different phrases in,” Bostedt says. “I tried to say the most egregious things possible just to see what the reaction would be. At least you’re having a good time with yourself.”

My colleague Ellen McCarthy, author of “The Real Thing: Lessons on Love and Life From a Wedding Reporter’s Notebook,” suggests trying a Zen challenge. Taking a deep breath and acknowledging that, wow, this is boring, can go a long way to accepting that is where you will be for the next 40 minutes or so. On that note, if you are really not having fun, it is totally fine to politely exit after that cup of coffee or first cocktail is drained.

Look around. Are there any conversation starters in the vicinity? On one boring coffee date years ago, there was a group of strangers next to us, playing a board game. I was so desperate for distraction that I asked if my date and I could pull up a chair and join their game. (This was in the pre-Tinder era, when strangers were more apt to speak to one another in public.) They said yes! As a group, we all ended up having a delightful time.

However, if you do not want to inflict your date on other humans: Is there a game on a TV somewhere? Can you turn your meetup into a football- or basketball-watching date just by moving seats at the bar? Go right ahead.

Avoid boredom by picking date spots you already enjoy. “You have to prepare for the likelihood that it will be boring,” Bostedt says. Which you can do by choosing to go somewhere you would enjoy on your own or with a friend. Bostedt recalls going on a date to the National Air and Space Museum, knowing “at least I would enjoy it even he was a dud.”

Remember everyone is boring some of the time. Some of the most interesting or funniest people I know are not telling riveting stories or eliciting raucous laughter in every single second of every conversation. Part of the joy of solid relationships, romantic or otherwise, is you do not have to constantly be “on” when you are together. You get to glimpse a person’s mundane and profound thoughts and bond with them through smiles and the yawns.

When boredom is the overriding character trait, either entertain yourself or get out of there as quickly as possible.


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