Obama’s former communications director Dan Pfeiffer describes receiving some excellent advice from the then-president in his new book, Yes We (Still) Can. Pfeiffer ― now the co-host of Pod Save America ― wrote that on his last day at the White House back in 2015, he was discussing his future plans to Obama and let it slip that he planned to move in with his then-girlfriend Howli Ledbetter.
“So are you guys moving together? This is the one, huh?” Pfeiffer recalled Obama asking. When Pfeiffer replied yes, the president reportedly said that the “advice [he] gives everyone about marriage” is to ask yourself three questions about your potential spouse.
“Is she someone you find interesting?” Obama said, according to Pfeiffer. “You will spend more time with this person than anyone else for the rest of your life, and there is nothing more important than always wanting to hear what she has to say about things.”
Questions one and two were just as weighty, though they required less explanation.
“Does she make you laugh?” Obama reportedly asked Pfeiffer.
Then, the conversation turned to kids.
“I don’t know if you want kids, but if you do, do you think she will be a good mom?” Pfeiffer recalled the president asking. “Life is long. These are the things that really matter over the long term.”
Luckily, Pfeiffer said he answered all the questions in the affirmative. (How awkward would that limo ride have been otherwise?)
“Howli is incredibly interesting and funnier than I am, and will be a phenomenal mom,” Pfeiffer said he told the president.
“Sounds like she’s the one. Lucky you,” Obama reportedly responded.
Pfeiffer and Ledbetter married in October 2016 ― one of four weddings Pfeiffer said he attended that year of couples who had met while working for Obama.
“Obama was always very proud of the hundreds of relationships that had sprung from his campaigns and his administration,” Pfeiffer writes in the book.
Given that the former president and first lady celebrated their 25th wedding anniversary in October, you’d be hard-pressed to find a better matchmaker.
As for how to stay married that long, Michelle Obama passed on some sage advice of her own while on Ellen DeGeneres’ show in 2015.
“What I’ve come to find is, you don’t sweat the small stuff,” she said. “The journey that we’ve taken together, the fun we’ve had, the challenges we’ve faced, the two beautiful children that we’re raising — I kind of give him a pass now when he leaves his socks on the floor or tells that story for the one hundredth time and wants us to laugh at it as if we first heard it.”
A relationship that’s always evolving and a lenient attitude toward dirty socks on the floor? Sounds like a recipe for success to us.