Dating Misadventures Pillows

Add a touch of humor to their home with pillows that poke fun at dating struggles. A cozy reminder that even awkward moments deserve a comfortable spot to unwind.

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 $44.00

Dating Misadventures Pillows 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 Prints

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

Dating Misadventures T-Shirts

Check out our witty t-shirts that celebrate life’s dating mishaps. Perfect for adding humor and personality to any casual wardrobe.