Dating Mishap T-Shirts

Celebrate the comedy of dating mishaps with our humorous t-shirts. Perfect for turning cringe into comedy and sharing a laugh with friends or that special someone.

Gimme a hot chocolate. On the rocks. Straight. Lady troubles? And how. Old Mr. Mort told me if I wanted to appeal to the ladies, I should watch some old black and white movies and do what those guys do. So I started jogging downstairs sideways like Cary Grant. I said "see!" after every sentence like James Cagney. I ran in place and yelled "whoop-whoop-whoop!" like Curly. All the girls loved it. But now I have four playdates scheduled at the same time! Not at all where I thought that was going.
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Gimme a hot chocolate. On the rocks. Straight. Lady troubles? And how. Old Mr. Mort told me if I wanted to appeal to the ladies, I should watch some old black and white movies and do what those guys do. So I started jogging downstairs sideways like Cary Grant. I said "see!" after every sentence like James Cagney. I ran in place and yelled "whoop-whoop-whoop!" like Curly. All the girls loved it. But now I have four playdates scheduled at the same time! Not at all where I thought that was going.

from $29.00

Dating Mishap T-Shirts Collection

Dating Mishap Mugs

Explore our collection of mugs that perfectly capture the humor of dating mishaps. Great for adding laughter to your morning routine.

Dating Mishap Pillows

Snuggle up with pillows that joke about dating disasters. Perfect for turning awkward moments into cozy memories.

Dating Mishap Prints

Decorate your space with prints that humorously highlight dating mishaps. A fun way to keep the laughs and good vibes alive in your home.