Q&A: Whitney Cummings on Hubweek and Why She’s Done Dating Bostonians

'I dated a Red Sox/Patriots fan, which can be very stressful.'

Whitney Cummings loves to visit Boston—she just doesn’t like dating people from here.

The comedian and 2 Broke Girls creator explained why she’s over Boston boys while previewing her upcoming appearance at Hubweek this weekend.

“I dated someone from Boston for four years,” Cummings says. “I spent a lot of time in Boston and a lot of time watching him yell at TV screens and YouTube Tom Brady.”

Despite her disdain for dating Boston bros, Cummings says she’s excited to be back in town to speak at Sunday’s panel event at Faneuil Hall. The discussion will be moderated by Harvard professor Michael Sandel and will also feature appearances by Arianna Huffington and Yo-Yo Ma.

Here’s what else Cummings had to say about returning to Boston, roasting Donald Trump, and more.

You’ve performed in Boston before and will come back to town for an event at Hubweek. How would you describe your experiences with the city?

I’ve performed in Boston quite a bit. One of my favorite venues is the Wilbur Theatre. I love me some Wilbur Theatre! I used to do the Comedy Connection back in the day, which I have a lot of nostalgia for.

I dated someone from Boston, which I will never do again. I dated a Red Sox/Patriots fan, which can be very stressful. So yeah, I dated someone from Boston for four years. I spent a lot of time in Boston and a lot of time watching him yell at TV screens and YouTube Tom Brady. I feel like I have a pretty close relationship with Boston, and a very good one.

So what should fans expect when you return to Boston for Hubweek?

I’m speaking on a panel with Yo-Yo Ma, Arianna Huffington, and Sherry Turkle. I’m just waiting for them to tell me that it’s a prank, like, “LOL, just kidding. We actually got someone who really knows what they are talking about.” I was so excited when I got asked because I am obviously a comedian. If you see my act, I talk a lot about neurology and questioning stuff, so it was really cool of them to see past [the image of] “She’s just a comedian, she must be an idiot.”

I’m excited to, if anything, if not bring wisdom to the panel, to at least bring a little bit of levity and to keep it funny. I have a lot of personal anecdotes from touring so much and being single so much that I feel I can help add some color to the conversation and keep it light.

Well, you’ll definitely bring some wisdom as well, considering you’re an Ivy League grad.

Yes! I went to Penn, so you know. I don’t know how much impact that has. I don’t think going there makes me better than anyone else. I definitely got in there just by some whim of luck, which is probably the same reason why I’m on this panel. Every 10 years I get a whim of luck and I get to be around Ivy League people. Maybe that’s what it is.

The panel is filled with people who’ve had a big influence on today’s culture. As a comic, is it cool to see comedy be a part of that bigger conversation?

I don’t think it’s something new. I think people like George Carlin and Richard Pryor were certainly not the first, but they started to get into political comedy and digging deeper than any news organization or a lot of journalists, frankly. I think there was some statistic where more people were getting their news from The Daily Show than from the actual news. Comedians are sort of leading the charge. I would rather my kid watch a Chris Rock special or a Lewis Black special or The Daily Show every night than watch the news at this point or go online to a news site. A lot of times, that’s just Kim Kardashian. What’s great about comedy is that you can tackle important issues in a lighter way like Michael Moore, who I actually consider a comedian in a way. His documentaries have been about 9/11, the election, health care, health insurance—no one would watch a documentary about health insurance unless it was funny.

Speaking of comedians tackling topics in the news, you once helped roast Donald Trump. Did you ever think you’d get the chance to roast a presidential candidate?

No. I didn’t. We were all like, “He’s lucky to even be roasted.” He was roasted that year because Willie Nelson canceled. We didn’t even want to roast him, that’s how insignificant he was to us at the time. Now, for him to be a presidential candidate—I say that as mockingly as possible in case this is in print—that it’s pretty hilarious to me. And my jokes still stand, I stand behind all of them.