Do guys succumb to cuffing season?

Last week we grilled JD Harris, owner of Glory Days Apparel, primarily on apps: What’s a good first message? Which apps are sketchy and which ones are useful? What should you put in your bio? If you haven’t listened to that episode yet, you can check it out here.

This week we wanted to dig a little deeper, so we covered the ideal first date, cuffing season, and more. Here are some of the key takeaways from the conversation, but make sure to check out the full episode below: 


JD broke down a few of his first date basics. They include:

– Stick to drinks for a first-time meeting. No fancy restaurants or long dinners.
– Meet somewhere public, and no pick-ups until you’ve met each other before.
– Keep the conversation light. “Pick up where you left off from the app or if you were texting,” he advises. If it’s going well, eventually you can dig deeper.

How soon into the date can a guy tell if there’s second date potential?

“If there’s any kind of connection you can tell, I would say, within the first 15 minutes.”

Women often feel the pressure to swipe more furiously when they start to become the last single friend in their group. Is it the same for guys? 

“I don’t think we get that kind of pressure from our buddies, but as soon as someone gets engaged or their spouse is having a baby I think we get that indirect pressure from the girlfriends like, ‘When are you next?’ A lot of my friends are starting to have babies and that’s great for them. There’s indirect pressure, like I kinda need to have a kid so I’m not doing it five years later and I’m not really part of the group anymore.”

Do guys succumb to cuffing season? Do you feel the need to hibernate with someone until patio drinking season rolls around once again?

“I mean, it’s much nicer to have someone there to watch “Elf” with you and do those kind of things with,” JD said. But though it’s nice to have someone around for these activities, he explains that a partner in Christmas movie-watching crime isn’t a total necessity for him, though he knows other guys beg to differ. Also, cuffing season definitely feels like a commitment through Valentine’s Day, so choose wisely.

When we had Andy Goh on The Margarita Confessionals, he brought up a great point: Guys often lack the emotional support in their lives that women have. We were curious about JD’s take on who dudes turn to during tough times.

“You can go to your buddies and they’ll help you, but it’s going to be a short conversation. They’re not listening intently and trying to figure out the more emotional side of it and it’s hard to open up.” He explains that his female friends, including friends’ wives and girlfriends, often become good sources of advice, and that they’re often who he relies on when a little venting is necessary. Hey, we all need someone to lean on.