So Here’s the Thing…: Notes on Growing Up, Getting Older, and Trusting Your Gut(28)

Doug didn’t have a laptop on the road, so sometimes he’d call me and have me dump his inbox for him.

He must have trusted me a lot. Of course I abused his trust. But of course he was abusing my trust first, and in a worse way, so here we are. If you feel you have to read your boyfriend’s emails, you kind of already know what’s in there. (For the record: It’s never crossed my mind to care about my husband DK’s inbox. I’m sure it’s all golf and…golf…) It became a real tool for me. I’d hear from people that he’d always visit a certain woman in Iowa…so then I’d look at his emails. (It never occurred to me, though, to think about what motivated people to alert me to these visits.)

What I found was that he was receiving messages and not replying. Boilerplate sexy messages. Descriptions of outfits, expressions of yearning. I somehow learned she owned red leather pants. And she was married. Which meant, to me, that he was responding via text message or some other medium.

When he got home, I called him out on it. He was cheating on me with a married woman in red leather pants!

He just looked at me and said, “My emails are none of your business.”

Was this a fair assessment? It’s complicated. But it shut me up. And I stayed with him.

I know, I know. I chalked it up to the campaign being crazy and high pressure, and we all do things we regret. But I also think that the haziness of gossip allows you to delude yourself and to take things with a grain of salt. I had no actual proof that Doug was seeing the woman in the red leather pants—maybe he really was receiving unsolicited emails? Not likely, but certainly within the realm of possibility. Right? Right?! The fact that he’d made me a target of gossip among my team should have gotten me angrier than it did at the time. I was always the boss over people my age; “Well, her boyfriend is cheating on her” is a great way to deflate the person you’re being forced to respect. When the women would say they couldn’t believe we hadn’t broken up, it was easy to discount them because I thought they were just taking out their resentment of me on my rumored relationship problems. I also wanted to prove the gossip wrong.

Still, after I realized his inbox was ground zero, I read his emails for months after that. (Yes: For some reason I still had access.) The straw that broke the camel’s back was a message from a woman who, for some reason, thought it necessary to tell him what nail polish she got at her mani-pedi. Come on.

But that’s not where this story ends! Oh no. By the time the Obama campaign rolled around, Doug and I had been broken up for years and had reestablished a great friendship. Which was good, because we both worked on the Obama campaign as well. I knew he was dating other people. I, however, was typically single. Until I wasn’t, sort of. One day he heard people gossiping that I was hanging out with another guy (let’s call him Joel), which made him feel like he wanted to get back together with me.

Vengeance? Not really. Instead of being an adult and saying to himself and his close friends, “She’s met someone and I’m jealous,” he decided he was in love with me. Soon, he was expressing this emotion to Obama. He and Obama were (and still are) close, and it was pretty early in the campaign, which meant he had more time for gossip. I should say, too, that we had all worked together for years at this point, and been through a lot. So a little bit of mischief was not unusual coming from POTUS.

We were all in Miami for a fund-raising trip when they—or maybe it was just POTUS—decided to implement their Get Alyssa Back! plan. I can’t remember if Joel was there, but at one point POTUS told me to take a car with him instead of riding with the rest of the group. I said sure; also in the car were Doug, Reggie, and Julianna Smoot. As soon as the doors closed and we started to roll away, making an escape impossible, POTUS turned to me and said, in his wisest fatherly tone, “Alyssa, this is foolish. You two”—gesturing to me and Doug—“should just get back together. You’re meant to be together.” Smoot was cracking up and pinching my thigh as I sat there silently receiving his counsel, confused and a little embarrassed. I mean, Doug was in the car.

I’m ashamed to admit this, but I ended up breaking things off with Joel. I got too distracted; I reasoned that if Doug was telling Obama he wanted to get back together, he must have really meant it. Seeing me with another man was just too painful! He’d seen the error of his ways! I decided we should get back together, too.

Well, no. Of course not. Because in the final act, email makes a valiant comeback.

A girlfriend of mine was on the debate prep team, and while she was in a meeting she noticed another woman on the debate prep team messaging Doug. The friend called me and tentatively began to relay the scene. “I love you,” she began, “and I know you were dating Joel, but I just thought you should know that Doug is definitely flirting with this other woman…” At first I didn’t know what she was trying to say. I assured her that it was all in the past—we had only JUST decided to get back together. But then she conveyed that she was watching the flirtation happen live, in front of her at that very moment.

Soon after, I had a few drinks with my friends at a bar, and I went nuts. I couldn’t wait any longer to express my displeasure. So I left my friends inside, went out into the street, called Doug, and started screaming into the phone. I can plead a little bit of campaign insanity, but I think the real moral of this story is that gossip giveth and taketh away and giveth and taketh away again. We really are better off as friends. (Which we still are.) (I swear.)2