1 of Obama's Top Aides Reveals a POTUS Story She's Never Told Before

As President Obama's former deputy chief of staff for operations, you better believe Alyssa Mastromonaco has some stories to tell. In her new memoir, Who Thought This Was a Good Idea: And Other Questions You Should Have Answers to When You Work in the White House, she shares a moving, funny, and sometimes heart-wrenching look back at the years she spent in politics and by the POTUS's side. We caught up with Mastromonaco to find out what it was really like to be one of the youngest people — and one of the few women — ever to hold her position in the White House, discuss sexism's impact on politics, and get her to share her personal hopes for what's next for Barack and Michelle Obama. She even told us a pretty charming story about President Obama's meddling in her romantic life she's never told anyone — and that includes her husband.

POPSUGAR: It's pretty clear from your book that you have a deep admiration and respect for Obama. Is it fair to say working for him made you a better person? Better at your job?
Alyssa Mastromonaco: I would say that Barack Obama not only made me a better person but made me better at my job. He's one of the most intellectually curious people you'll ever meet and really brings that out in other people. When I first got to the White House, I was super anxious all the time about not knowing the answer to every question. And Obama was actually the person who let me be me. He was like, "Alyssa's not the person who wears the Ann Taylor suit. She's not the kind of person who always says the exact right thing." And I'm a bit of a wild animal. I brought a different perspective, and I was a little bit more irreverent and casual.

PS: I teared up when I got to the end of the book and read the passage about him calling you after your beloved cat died. It was well after you'd resigned from your White House post.
AM: Just so you know, I had to reread that portion of my audiobook three or four times, because I cried every time. I, more than anybody, saw all the things that were on his plate every day. I felt other people maybe didn't realize how much a note meant that he wrote them or a phone call. But I saw his thought process behind the few moments of free time he had and how he used them. So, I knew that him taking the time to call me meant he really cared and really deeply understood how upset I was. That's what made it so meaningful.

PS: I love the anecdotes about Barack trying to set you up. It happened more than once, if I recall!
AM: There's a story I tell [in the book] about leaving Iowa, when he's telling me to email a guy that he said was into me. There was a thunderstorm, and we ended up having to drive from Ames, IA, all the way back to Chicago. So Gibbs [then Obama's senior adviser] and I were in the backseat of the PT Cruiser, and Obama kept turning around like, "Email him. Email him right now. He was not a bad-looking guy."

PS: So, wait — you were driving Senator Barack Obama around in a PT Cruiser?
AM: He was in a PT Cruiser. It was gray.

PS: What's the biggest way you saw the presidency and everything that comes with it — the responsibility, the celebrity — change Barack and Michelle?
AM: I think the external perception made them much more aware of making sure they stayed themselves. We win and it's super heady, and then a couple months later you are awarded the Nobel Peace Prize, but the one thing that we all believed — and that the president believed — is that you can never really buy into your own hype. Because as much as the world loves you one minute, they can be way down on you the next. I think that you would say if you looked at both of them, they kept it pretty even-keeled throughout the eight years, and he expected the same of us.

PS: Do you keep in touch?
AM: Oh, yeah. I saw them both in Chicago [on Jan. 7], and I saw the president at Marvin Nicholson's wedding down in Florida [on Jan. 10].

PS: I know a lot of people are very excited to see what he and Michelle do next. What do you hope to see them do?
AM: There are so many kids in the world who have only grown up knowing that an African-American first family is a part of life. I think the next couple of years are going to be pretty hard to get through, so I hope that they're super visible and that FLOTUS keeps up all of her work with young women.

PS: You explicitly say part of your motivation in writing this book was to get more women interested in pursuing political careers. What in your own experience proved the need for that?
AM: I didn't have a ton of role models back in 1998. So, when I was looking to get in, it was really just looking up at all the men who were out there. When you're not seeing women — when you're breaking into anything — it's like, "Well, this is what the men do and how they act, so we're going to just emulate that behavior." I wanted young women to know that I was very lucky that I worked for people who literally let me be me. If I had ever been anyone other than me, I would have come off as a fake, a phony, a fraud, and never would have gotten where I ultimately ended up. You can be yourself and be in politics, and they should know that. That was kind of why I wanted to do it — because I didn't see any freaks in politics like me.

PS: Was there a particular moment you remember facing blatant sexism in the political world? How'd you handle it?
AM: There was a moment. It was the very beginning of the Obama campaign in January or February of 2007. I was asserting myself, and someone on the campaign — who wasn't David Plouffe or [David] Axelrod or anyone like that — but someone came to me and said, "You better get in line, because the people in South Carolina are just going to think you're a real b*tch." It was a man. I was just like, "Wow." I didn't say it, because I was so stunned, but in my head I was like, "Wow, and you're a real d*ck." That's the one moment I can really think of where I was like, "I don't think anybody would have said that to one of the guys." I wasn't even being aggressive. They were just wrong, and I told them they were wrong.

PS: I'm sure you have a fascinating perspective on how sexism impacted the 2016 election and Hillary Clinton — who you worked alongside when she was secretary of state.
AM: I don't think that Donald Trump treated Hillary any differently than he treated Ted Cruz or Marco Rubio. He is a deeply disrespectful person who didn't have enough reverence for the office he was running for to act humane. I never like to oversubscribe to sexism. I'd love to say, "Donald Trump is just sexist." And I do believe he's sexist, but I also believe that he also treats anyone who is his opponent in a very insane and disrespectful way. Saying, "Lock her up!" — which is insane — and calling him Lyin' Ted and him Little Marco . . . it's all really bad.

PS: What was it like from your perspective to witness the entire election cycle, this time from the outside in? Did you have FOMO?
AM: It was really hard. But the whole time, I think that we all thought that she was really going to win. So, you didn't feel that kind of FOMO like, "Oh my god, I should be there because I could make such a difference." I think we all kind of thought it was handled, and then, when she didn't win, I did feel like, "Oh, god — now I really need to be an activist." I want to be out marching all the time. I want to wear "Feminist AF" t-shirts.

PS: How did the Obamas seem in January when you saw them? I know Michelle Obama has been pretty open about feeling a sense of relief about being able to step away from the White House.
AM: The times I saw them, they were pretty nostalgic. I'll tell you two things: if you look at the video of the farewell speech the president gave on Jan. 10 in Chicago, and you look at the very end, you can tell he's taking in the moment. The thing that I think is so depressing, fundamentally, about Donald Trump is that he doesn't appreciate what's happening right now. He doesn't seem to think it's an honor. He doesn't seem to understand why we're actually super blessed to have the government we have. I also don't ever get the sense that he loves Americans. If you look at POTUS [Obama] — and I will always call him POTUS — I think that what you saw during those eight years, and in those last few weeks, was that they really love people and they are going to miss them. And that they deeply appreciate the opportunity they were given.

PS:What's your advice for young women who might be interested in getting into politics but are feeling deterred — whether it's because it's still a male-dominated field or they just don't know where to start?
AM: Find someone who you really believe in — that can be at a state level. The one thing I can encourage women to do the most is to start at the state level. It is the biggest reason that the Democratic party is behind. Women generally have to start building the bench, and right now our bench is a little thin. If I were to ask you who you think will run in 2020, we're like, "I don't know. Maybe Elizabeth Warren? Maybe?" Because there aren't five or 10 people. I would encourage young women to find that person, give it your all, and leave it all on the field. The one thing I have found is that if you are sitting at a table, most women will want to only give their opinion only when it's almost fact in their mind — whereas dudes will pontificate a lot more. And I will tell you, I've started pontificating a lot more, which is very satisfying. They should not be afraid to speak.

PS: What's a piece of advice, or something Obama said to you over the years, that really stuck with you?
AM: Here's something nobody knows. When I had been dating my husband for a while, the president said to me, "When is he going to put a ring on it?" And I was like, "Oh, come on. We are so busy. We don't need to think about that." He said, "He needs to put a ring on it because you're worth it." And the thing is, I'm not even kidding you, it was about a week or two later that we got engaged. I've never told that story to my husband, either. It would be news to him. Also, what, are you going to go back to your boyfriend and say, "The president told you to put a ring on it"? The lamest thing ever.