Bohler Books

“It’s better to be boldly disappointed than to meekly wonder what might have been. Ask her. What’s the worst that could happen?” asked my friend, Jim.

“The worst that could happen,” I said, “is she gets awkward around me after she rejects me, and it ruins this budding friendship we have. I enjoy spending time with her, and I don’t want to ruin that.”

“Good. You’re clear on the cons; now the pros.” Jim said, “What if she says yes; what’s the best that could happen? What do you stand to gain?”

“Potentially, a romantic relationship with the most amazing woman, who leaves me feeling happier than I ever imagined possible whenever she smiles at me or tells me about her day.”

“If you think she likes you, you’ve got to try,” insisted Jim, “You owe it to both of you.”

“That’s the thing. I don’t know. I can’t tell,” I replied, “She’ll tell me about her favorite movie, restaurants she wants someone to take her to. She told me she’s scared to join dating sites, and wants to meet someone in person.”

Jim threw me a sad smile, “Seems like she’s trying to hint that she likes you.”

“Isn’t that the sorta stuff she’d say to her gay best friend, though? How do I know she doesn’t just see me as a friend, someone ‘harmless’ she can talk to?”

“You ask. You know what’s the worst kind of regret? When you’re talking to her years later, on social media, when you live in different states, thousands of miles apart, and mention that you like her, and she says, ‘What the hell? Why didn’t you say something back then? I had such a crush on you! I totally would have dated you!!! I always thought you weren’t interested in me. If we ever wind up in the same place again, you gotta hit me up.’ It’s the absolute worst. You need to ask.”

“You’ve had that happen? Seriously?” I asked.

“Believe it or not,” replied Jim, “it’s actually happened three times. Not the exact same words, obviously, but the same story.”

“Wow. That’s crazy.”

“It’s a buttload of suck. I’m single because I can’t seem to ask a girl out before life circumstances destroy my chances. Learn from my mistakes. Don’t be like Jim. Ask.”

“I think I will, when I get a good chance to bring it up. By the way, who said that quote?”

“What quote?”

“What you quoted, earlier, ‘It’s better to be boldly disappointed than to meekly wonder what might have been.’ Where’d you hear that?”

“What? I’m pretty sure I said that, like five minutes ago. I don’t think I heard that anywhere. It’s just life, man. Just my experience.”

“You give good advice, Jim,” I said.

“Yeah? Do I? We’ll see,” said Jim, “Maybe, one day, I’ll take it.”