The Wild Reason Why Chelsea Handler's Dating Life Costs Her So Much Money

Chelsea Handler is going where few celebrities have gone before: the truth. On each page of her new memoir, Life Will Be the Death of Me, the comedian, actress, Netflix star, writer, and overall multi-hyphenate host tracks the journey of personal growth she was prompted to launch after the election of Donald Trump. Inevitably, that journey also leads inward. In addition to touching on the quirks of the celebrity lifestyle, privilege and political activism, Handler opens up about the loss of her brother, Chet, and her family life.
Naturally, since she's going all-in on the candid front, she also dishes about love. Below, a conversation with Handler and her psychiatrist, Dan, about the state of her dating life — including why she's so drawn to older men, and why she sometimes pays the younger ones.
This excerpt has been published with permission of Penguin Random House. Life Will Be the Death of Me is available on April 9.
“Tell me about the kind of men you do like,” Dan said.
“I like older men a lot, and I’ll tell you why it’s become a problem: because now I’m 43, and older men are getting really old, if you catch my drift. So now I have to scale back my margin and lower the difference of age that’s most preferable to me, which used to be 20 years. This is what is referred to as ‘thinning the herd.’ That is why I have the feelings I do for Robert Mueller.”
“I’m sorry?” Dan asked.
“I have strong feelings for Robert Mueller. I find him incredibly sexy, and I know why. It’s because he has shit together, and my father never did. I get the psychology behind it, but then I’ll hook up with younger guys who are absolute and utter messes — whose lives I turn upside down even more, and who I then lose interest in. These relationships are based solely on their looks and their bodies. It’s completely reckless behavior when I think about it.
“My interest in younger men is new, but they have to be grown men. They can’t be growing. I want to be thrown around on a bed (in a loving way) while also being told to shut the fuck up when I’m being obnoxious. I know that’s not a popular thing to say in the current climate, but that’s what I like. Young guys won’t do that. I want to be dominated — by an older man — but in the past couple of years, I’ve had no choice but to start dipping into younger guys just because that’s what the Lord keeps putting before me."
“The real problem with younger men is that I am always the first one to lose interest, and in the past, it has cost me tens of thousands of dollars,” I went on. “I’ve had a few younger guys in my life, and each time I convince myself I’m not going to get sick of them — like a new album you listen to repeatedly. You know if you abuse an album and listen to it too many times, you’re going to get sick of it, but part of me always thinks this album will be different.”
“Why does it cost you money?” Dan asked.
“Because I usually upend their lives in some irreparable way — like I come in and out, and I don’t take them seriously, and just want to have fun — and then, when they get serious, I just want to do anything that will make them feel better, so I usually just give them money.”
“What?” Dan looked horrified.
“I think we do.”
“Yeah, I know you probably think we do, but IAM.” I may have winked at Dan when I said this, but I hope I didn’t. “Identification. Awareness, Modification. I’m going to modify, so let’s keep talking about relationships, because I want to know what’s wrong with me. Or what’s not wrong with me. Let’s ring that bell, shall we?”
“You shouldn’t be giving men money just because you are breaking up with them, whether they got fired or not. You’re not forcing them to sleep with you, are you?”
“No, Dan. I’m not raping men."
“So, why are you paying them?”
“Because, I’m just not thinking about their circumstances and that they could lose their jobs. So, if that happens, and it has happened, I try to ameliorate the situation — with money.”
“Do you understand that that behavior — paying someone to break up with them — isn’t necessary?”
I needed to switch gears. I told Dan that I also go for very long periods of time without any male interest or sex, and I’d prefer to be having more sex.
“You don’t get hit on by men?”
“No. Not typically. Not in America. I think I’m just one big boner killer. Older men like me, because they’ve seen it all and they probably find it refreshing, but men my own age are definitely not interested.”
“Probably because I’m loud. It’s obnoxious. People are scared of me.”
“You say that often.”
“I hear it often.”
“People tell you they’re scared of you?”
“Dan, I’m loud and brash. Certain people find that off- putting. Most straight men find that off-putting. This isn’t hard for me to understand. Why is it hard for you to understand?”
“It sounds like you’ve worked your entire life to make sure that you wouldn’t get hurt again.”
“But, I have gotten hurt. I’ve had my heart broken."
“And what did that feel like?”
“It was awful. I was completely out of control — like a madwoman. I get distracted with love, and I’ve let it take over before. I’ve done unreasonable things, like checking a guy’s phone, or acting out of fear and jealousy — all the qualities I’m not interested in having ascribed to me. It’s just so much safer to be single. I just get more done when I’m single. So, yeah, let’s talk about that.”
“That’s your doing, not your being.” I pretended I didn’t hear that.
“So, is that Chet too?” I asked Dan. "He’s certainly getting a lot of airtime for a dead guy.”
“I don’t think you’ll allow it. I don’t think your subconscious thinks it can take another letdown. You are most likely actively making sure that you are preserving the only reliable thing in your life.”
“Which is?”
“Yikes,” I said.
“Do you think you’re capable of being in a loving, caring, relationship with a man, knowing that if something terrible happens, and he dies, that you will be okay?”
“No. No. No. No one can die.” Dan stared at me. My body reacted as if I had been Tasered. The tears filled my eyes and spilled down my cheeks. Once that sentence left my mouth, I was able to hear myself. Not what I said, but the tone with which I said it and the age of that voice. The 9-year-old.
“I can die, but no one else can die. It’s enough already with death,” I said, snapping back to my present-day self.

More from Books & Art

R29 Original Series