Dating Expert Wannabe T-Shirts

Explore witty t-shirts for your aspiring dating guru—funny, clever designs that showcase their love for match-making and relationship advice.

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.
View Product

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 Expert Wannabe T-Shirts Collection

Dating Expert Wannabe Mugs

Looking for more love-themed mugs? Discover a wide range of charming and humorous designs perfect for your dating enthusiast.

Dating Expert Wannabe Pillows

Find cozy pillows with playful and romantic designs, ideal for your aspiring dating expert to add charm to any space.

Dating Expert Wannabe Prints

Browse our exclusive prints celebrating love and connection—great for inspiring your dating expert wannabe every day.