Ask Lemmy
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Do something or go somewhere neither of you has been or done before.
If it's enjoyable for both of you, you win. If it's not fun, you get to bond with each other over not liking it.
People naturally bond when experiencing something together for the first time and feel the same way about it. If you feel the opposite about the experience, then you know you are less likely to be compatible.
The most important part is to be honest about how you feel about the experience, and be honest immediately if you don't like it. "This is terrible, right?"
My marriage is the result of several weeks exploring the town. Other dates were not honest about not liking something, and the relationship didn't last. Wife to be felt the same way about places we tried as I did. If it was a terrible experience and we both thought so, it would bring us closer together just as much as a positive one. In fact, the terrible experiences were sometimes the best because we would laugh together about how bad it was. It's like taking a compatibility test.
Something new is good advice.
It's temping to do something familiar to minimise the "risk" of a bad experience, but that's false safety.
It's human nature to get defensive of what we already know we like, and it puts the other person in a difficult position too where they may feel forced to pretend, or to keep their genuine opinion quiet.
Something new puts you both on an even footing, leaving neither disadvantaged, and that's cool. And - as you say - even if it's terrible, at least you can both laugh about it.