These Boots Are Made For Walking

Last night my husband came home with a huge box and a grin about the same size. The outside of the box was covered in a western cowboy scene and low and behold, inside that box was a pair of size 14 cowboy boots. Fancy cowboy boots. Note, these are not the boots above, but just an image for your mind. He and a friend had been shopping for a pair about a month and now the blessed day had finally arrived when they were delivered.

He watched me as I took the boots in. I could tell it was a crucial moment so I tried to remain neutral and nod like these were the best pair of boots I'd ever laid eyes on. It didn't work and Joey saw through my sham. Dang it, why do I have to be so expressive?!

And then it came. "Do you like them?" Oh dear. Caught between lying and bursting his bubble, I proceeded with caution. "Well, you've been looking for a pair of boots and these look like they'll fit the bill!" "But do you like them?" Umm, well, errr, you see I'm not the best judge because I'm not the biggest fan of cowboy boots unless you are in full out cowboy gear."

This didn't go over well. "So, you're saying you don't like them." And then it just came out: "They look like Herman Munster shoes." There. I said it. The cat was out of the bag. And so was Joey. He immediately started packing the boots up in all their western glory. "No, no, wait! If you like them then that's what matters!" Too late. I had officially hurt his feelings.

To make matters worse, he said "I'm going to take them with me to the gym when I meet So-and-So tonight and see what he thinks about them." The Ultimate Shame. See, So-and-So is this new guy that Joey has been what I like to call "Man Dating". It started with working out and bike riding together. Then it was a few shopping trips to Bike Barn. Shopping for boots. Watching football. And my favorite, a movie. Now, I will say that there was a third guy at the movie. I wonder if he felt like a third wheel?

Anyway, I felt like I was reliving a scene from a nineties movie where there was That Guy who was dating the Mean Girlfriend who tells him how to dress all the time and disapproves of everything he does. And all the while there's this Other Not So Popular Girl who really likes him and loves everything that he does so he ends up going back to her for encouragement. In truth, I'm usually the Other Not So Popular type, but in this instance I was The Mean Girlfriend. This was a long run-on paragraph, but are you tracking with me at all? I can't believe I was the Mean Girlfriend! I always loathe that character!

My question is: what is the line to being honest? How do you know when someone wants the truth or when you should be an encourager?