Dating Misadventures T-Shirts

For those who wear their dating stories on their sleeve, our humorous t-shirts are great conversation starters. Celebrate overcoming or simply surviving your latest romantic misstep in style.

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 Misadventures T-Shirts Collection

Dating Misadventures Mugs

Explore our collection of amusing mugs perfect for anyone who's ever had a dating misadventure—funny, relatable, and sure to bring a smile.

Dating Misadventures Pillows

Discover pillows that turn dating blunders into home decor humor. Cozy, funny, and perfect for sprucing up any space.

Dating Misadventures Prints

Browse our humorous prints highlighting dating misadventures—ideal for decorating or giving a light-hearted gift to loved ones.