David Spade has this sort of self-deprecation about him that we can’t help but love, but he’s still living the dream. He’s rich, has dated his share of goddesses over the years (Heather Locklear, Lara Flynn Boyle, Jillian Grace) and had rumored flings with the likes of Nicollette Sheridan and Pamela Anderson. His fictional life? Even better. Though he started out the nerdy sidekick of Chris Farley in Tommy Boy and Black Sheep, Spade’s pasture became a whole lot greener when he portrayed the ultimate bachelor who bedded a different beauty every night on Just Shoot Me and Rules of Engagement.

If you glamorize his lifestyle, however, he’ll take your compliment but quickly laugh and say that his only attractive quality is that he’s semi-normal. “I know it might be cooler to be crazy like Bieber or Chris Brown and have drama going on every day and shit in the papers,” he explains. And when it comes to his lady luck, he’s the first to explain that he’s “not the guy they beeline over to fuck when they see [him] in a room. It takes a while for them to go, ‘Oh I’ve talked to him a few times. Oh he’s not that bad.’”

Spade is currently setting his sights on venturing outside of his norm. In his upcoming film The Do-Over, also starring Adam Sandler, he even plays (are you ready for this?) a married man. Before that, producers wouldn’t even allow him to attempt an on-screen girlfriend.

Playboy caught up with Spade to discuss his recently released memoir Almost Interesting in which he recounts everything from losing his virginity to the array of ridiculousness that fame has brought into his life. He tells us about the infamous dating advice that his mother bestowed upon him and why his neighbor sued him; he also tackles our Lucky 7.

What prompted you to let all the skeletons out of the closet and release Almost Interesting?
Oh my stupid book you mean? I was going to do a book during Just Shoot Me just for fun. All these comedians do it at some point. Now I thought, I have time and I can focus on it and not just get a ghostwriter. It was better because I could do it in my own voice, and I know everything in there is at least from me. Because sometimes [the editors] would even try to guess my voice and write a few sentences to connect some tissue together. I would immediately go, “Ahh, I didn’t say that shit!” So good or bad, it’s me.

You have The Do-Over coming up next. Is this the first time you’ve played a married role?
That’s a good question. I feel like it is. It might even be the first time I had a girlfriend. Even on the big things like Rules of Engagement, no girlfriend, I’m always single. Grown Ups movies, single; Just Shoot Me, single. There was a pilot last year I liked and they said, “Well you’d be married. No one can picture that.” I said, “Is it that weird, guys?” But The Do-Over is going to be great. I think you’ll be happy with it. I play a married guy with step-kids and it’s my favorite thing I’ve done in years.

Do you enjoy playing the bachelor?
I think it’s funnier to go on stage and have things go wrong. People relate to that. And everyone does married jokes, but I think it’s so much fun finding stuff about being single. And even in the book, I was trying to get into stuff about Periscope and Snapchat and Tinder. Every day, I’d hear crazier stories and that’s funnier to me than just the boring, like, “Well, wife came home. She doesn’t cook. Kids are driving me nuts.” That’s just funny to watch in real life. It’s a calmer life in real life I’m sure, most of the time. But in the movie and TV, it’s funny to play single.

What’s the secret to staying single at 51? Do you think you’ll ever settle down?
Gosh. Single at 51! You just hit me right between the eyes with that one. I never really say it out loud. I think it’s definitely something people feel embarrassed about, especially girls, when they are single – even if it’s for fucking 4 days! There is something so weird about the fact that you can’t say you are single and be proud of it. Because most people say it and they are not proud of it. They are like, “I’m so happy to be single!” and they are bawling at home. I’ve actually gotten comfortable with it just because it was so overwhelming and still is. When you get entangled in a very serious relationship and you take someone else’s whole life and problems on, well, they take yours too; it’s a two-way street. I’m barely figuring out my own shit. I think that’s what happens when people get married or have a serious relationship: They either need to be propped up by someone or they can’t even handle their own problems and try to fix someone else’s, and that’s where the fights start. It’s hard to get it right.

I’m sure many ladies out there have tried to snatch you up over the years.
I don’t know how snatchable I am. I do think that my mom said, “If you live in Hollywood, just don’t be gay and you’ll get married right away.” Because she heard everyone was gay out here when I moved out here. And she goes, “Just be a normal person.” I have to say, my only attractive quality is that I’m sort of normal. And I know it might be cooler to be crazy like Bieber or Chris Brown and have drama going on every day and shit in the papers, but I think the only people that are gravitating towards me are thinking that I’ve got a little bit of money coming in, I’m not a super drunk or a drug addict. I’m not very dramatic. So it sounds boring on the surface and then it’s boring when they meet me so I don’t really know where the upside is. I don’t really know where I was going with that. But I tell jokes. So at least I try to be fun.

With your roles on Just Shoot Me and Rules of Engagement, you’re seen as the guy that is living the dream. What have you learned in real life from playing these parts? Is there a go to pick-up line or a move that always works?
No. There’s not. I think just don’t get too old and don’t get too fat. Because I think at a certain point, you just get knocked out of the game. I know the living-the-dream thing, but there is a grass-is-greener thing. Some of my friends are super neighbor guys. They have everyone over from the neighborhood; they have the wife and kids. I’m a little envious because it reminds me of growing up when people would have you over to their houses and you would go eat over there and go hang out. I have none of that. I live on a hill with neighbors that I haven’t met once in my life. The only guy I know lives across me. He moved in and said, “I’ll probably sue you because I want you to cut your trees down” and I was like, “Well alright. Nice to meet you.” And he followed through with that. And I live on a hill so I can’t really walk around. And people know me so it’s weird. I go to my friends’ houses to be normal and see their neighbors but everyone gets thrown off a little bit. I think it’s just a different life that has a lot of positives but there are a few tiny things that are a little weird about it.

What’s the secret to landing that Rule of Engagement type of show?
I don’t know how I stumbled into that. Tommy Boy and those movies, I wasn’t really a cool single guy. There was a time when I was just sort of a femme feminine snarky guy that could have been gay in some of those sketches. I played the receptionist and then I was the nerd smart friend of Farley in some of those movies and then I got Just Shoot Me. That sort of broke it open into “Let’s have this guy date on the show and see how stupid it is.” And that played well I think and then Rules of Engagement happened. It’s hard to get out of that. The Do-Over is the first time I’m getting a chance. It’s by no means some groundbreaking role like Sarah Silverman did, but it definitely is a little different for me, which counts as a lot.

What was your first exposure to Playboy?
Marianne Gravatte. Back then. I was probably seventh or eighth grade when I took a Playboy and really dealt with it the way you’re supposed to. When I think of Playboy, I think of pubes. Remember? I think that’s how we categorized it. They all had a triangle bush and I was like, Hip, hip, hooray! And I know somewhere along the way it went to hardwood and I wasn’t as happy about it. But I think it’s coming back.

What movie scared you the most as a child?
Well I never ever will see a scary movie. I will say that. I didn’t see Halloween. I didn’t see The Exorcist. I was so scared all the time that I never got through those. So probably a piece of any of those. I saw Tommy and I got scared, the movie about the Who. I was scared about that. Even my mom was like, “Alright, you pussy. Jesus!”

If you were on Death Row, what would your last meal be?
So many choices! Maybe pizza because I love it so much and I don’t eat it as much. Pizza and a Big Mac meal. Yeah, just go out big! Go out with diarrhea.

What was your first car?
A ’62 Volvo for $300. I look back and even that was too much. It was such a piece of shit.

What is your pop culture blind spot?
Kylie Jenner is curious to me. I’m not sure if she’s ruining America. I’m deciding this week. I’ll let you know!

What’s the first song that you knew all the words to?
Let’s go with “Happy Birthday.” I probably knew the words to that at like 4.

What’s the biggest lie you ever told?
I remember telling kids at school that my dad had a silver Porsche. He came around like once a year. And they were making fun of me because he never came around and I was like, “Yeah well he’s got a silver Porsche. You’ll see!” He didn’t. That’s like a lie that makes you cry!

Why should people go see your standup? The standup is still actually pretty funny I have to say. But we might switch this answer to No. 6, which would be the biggest lie I ever told. I’ll go, “My standup is great. See question 6.”