Some Friendships Need to Go with Issa Rae [From the Archives]

IMO with Michelle Obama and Craig Robinson - Higher Ground

In this episode of IMO with Michelle Obama and Craig Robinson, the hosts explore the complexities of friendship, including how fame and life changes can strain relationships. They welcome

Key takeaways

• Friendships evolve over time, and maintaining deep connections requires intentional effort, especially as life changes with fame or personal growth.
• Many male friendships are more transactional—based on shared activities rather than emotional depth—which can lead to less impact when those relationships end.

Main topics

• The evolution of long-term friendships
• Impact of fame and success on relationships

Notable quotes

"I just wanted to get this off my chest. This is the way that I really valued you. I'm sorry I didn't show up for you in this way."

"If you really feel badly about it, write her a letter. But don't expect a response."

Conclusion

Friendships, like life itself, are dynamic and require care, honesty, and sometimes

Transcript preview

Speaker 3 (0:00) Like the crisis would Speaker 4 (0:01) require an emergency session. Oh my God. Like somebody's on a train. Yeah, flying. You know, Speaker 3 (0:06) there's movement. And you got to kind of Speaker 4 (0:09) deal Speaker 3 (0:09) with the crisis. Speaker 4 (0:09) Yeah, I was like, we're coming. We're coming. It's a crisis. Speaker 3 (0:12) My friend's dog died. We were all... there at the house bringing her favorite snack. Like, this is... Took off work. That Speaker 5 (0:20) is Speaker 3 (0:20) a Speaker 5 (0:21) script. That is something that you could write on television. Playing Speaker 3 (0:26) and doing a text like, you know, she's not going to be good. Like, she doesn't need this right now. You know? Speaker 5 (0:31) Right, right. You know what's so horrible about that is guys will be like, damn. Yeah. That's it. Not a crisis. Honestly, not a Speaker 4 (0:39) crisis. Sorry. Send a dog of OGs. Or dude, I didn't know you had a dog. Yeah, what? Where'd you get a dog? Speaker 5 (0:47) Okay. We are here, man. Speaker 4 (1:01) Hey. Well, hi again, you. It's you again. Oh, I like your, is that pink? Speaker 5 (1:08) It's, my wife called it coral, but it could be pink. Yeah, it is Speaker 4 (1:11) coral. And it's Speaker 5 (1:12) a Speaker 4 (1:12) little pleated. This is breaking out of the, you know, basketball thing. Watch out now. And Speaker 5 (1:19) that little Speaker 4 (1:19) collar. Okay, I see you, Craig Robinson. I Speaker 5 (1:24) am thrilled that you like my clothes. Yeah, nice. See, Speaker 4 (1:27) you Speaker 5 (1:27) guys, it's hard being this one's brother. I don't have enough closet space. Speaker 4 (1:33) You know, you don't even need much closet space, but you're stepping out. You're stepping out. Thank you. What's new and exciting? Speaker 5 (1:41) Well, I got to tell you, while we're out here in L.A., Speaker 4 (1:45) Rivian Speaker 5 (1:46) hooked me up with a vehicle. tool around in since you won't be able to drive one since you Speaker 4 (1:52) don't drive. No, no, I'm starting to drive. Really? Yeah, I can drive. How's that? Speaker 5 (1:58) How's the Secret Service letting you drive? Well, it's Speaker 4 (2:00) a secret. You could take me for a spin. They'll Speaker 5 (2:03) let me take you for a spin? Speaker 4 (2:04) Don't Speaker 5 (2:05) you Speaker 4 (2:05) remember when I came to visit you in Milwaukee and the boys wanted me to pick them up from school? Speaker 4 (2:13) We did. And Speaker 5 (2:14) you tooled up in a motorcade to their school? In Speaker 4 (2:16) a motorcade Speaker 5 (2:16) in the Speaker 4 (2:16) pickup line. They were just like, meesh. I was like, yeah, yeah. Speaker 5 (2:21) Four cars deep in the pickup line. Four SUVs deep. That was so much Speaker 4 (2:25) fun. I'm sure their friends were like, what the heck? Speaker 5 (2:29) And then you roll down the window and it's you. They're like, meesh. Speaker 4 (2:33) I'm like, get in. And don't touch the guns. I do remember that. Speaker 4 (2:42) Oh, my goodness. But so we're talking about friendship today. Yeah. Speaker 5 (2:48) And people know by now that you and I are like have been best friends since you were born. Speaker 4 (2:54) Yep. Because it couldn't happen before then. No, it could not Speaker 5 (2:57) happen before then. But my first question to you is how many of your friends now were your friends when you were little? Speaker 4 (3:08) Like the little, little, I don't keep up. don't get a chance to keep up with the folks from little, little time. Although, as folks know, mom recently passed and a lot of people came to the funeral. And two of my girl girls from grammar school, the Gores, Pam and Nikki, and they had a little sister, Gina, but they came to the funeral. And it was funny, we got a quick second to talk, but it was almost like I hadn't I hadn't missed a minute with them. But so we vowed to keep in touch. But outside of childhood, I can say that I have at least. almost at least one good friend or more from every aspect of my life. So what I found is like one of, you know, my best friend, roommate, who you know, Angela from Princeton. She was my roommate. She's my girl. Always talked to her from law school. My friend Verna just went to her house for lunch. just the other day. She's in DC, you know, and then there are my mom friends because as I got married, but then even before then that was Pam. She was more my professional friend when I was when we were grownups and had jobs at law firms. And, you know, I could go on and on like that. And the other thing I made a point of, because one of the things that you said when Barack won and we got to the White House. One of the things we were like, no new friends, that's it. And I was like, ah, you know. I did say Speaker 5 (4:49) that. Speaker 4 (4:50) Yeah, you were kind of joking, but it was important for me in the normalcy of my life to be able to, or to keep my life normal, even in those unusual circumstances, to continue to expand my friendships. So that's a long answer to say. Yeah, I do. I keep making friends and I keep up with my friends. Right. Speaker 5 (5:13) And this today's show is talking about differences with those friends and falling out of friendship with Speaker 4 (5:20) good Speaker 5 (5:22) friends. And I'm just thinking, see, guys are a little different. Their friendships are more transactional, right? What do you Speaker 4 (5:32) mean by that? Speaker 5 (5:32) Well, what I mean is... After sort of grammar school and high school where you're sort of friends with people because you're developing your group and your personality and your character, most of the time after that, you make friends out of the necessity of wanting to get something done, whether it's a business idea, a business venture, a sporting event. You've got four tickets to a game and your significant other doesn't want to go. All right, I'm going to take three friends. Would you just make a friend? It's Speaker 4 (6:05) like, okay, let's be friends. Come to the game with me. Guys do that. That's why y'all are broken. We are not broken. Speaker 5 (6:12) But we don't go as deep. Speaker 4 (6:17) Yeah. Speaker 5 (6:18) So if something happens, we're not as hurt. Speaker 4 (6:22) Is that what meant? Y'all scared? Nobody said it was scared. I don't Speaker 5 (6:29) want Speaker 4 (6:29) my feelings hurt, so I can't know you. Speaker 5 (6:32) It's just a function of how we socialize with each other. And like you, I have all of my friends I could not talk to in Speaker 4 (6:44) a Speaker 5 (6:45) year or I could talk to every week. And the relationship is... Speaker 5 (6:51) mostly the same. Speaker 4 (6:52) That's because y'all don't talk about nothing. Well, we don't. You're right about Speaker 5 (6:55) that. It's hard to go Speaker 4 (6:57) deep. You know Speaker 5 (6:58) when we go deep? Uh-huh. Is when it's too late. Speaker 4 (7:04) Deathbed. It's like, whew. Speaker 5 (7:06) Bubba, I wish I had asked Speaker 4 (7:08) him about his family. We're Speaker 5 (7:09) getting a divorce. Oh, yeah. And then there's some tragedy. It's like, why didn't Speaker 4 (7:13) you Speaker 5 (7:13) say anything? I didn't say anything because I didn't want to burden you. And I was going to thug through it myself. But today's show, we're going to talk about, you know, sort of falling out of friendship with close friends. Speaker 4 (7:27) We are a company. Speaker 5 (7:28) We do have company. And I can't tell you how excited I am for this company because as I told her in the green room, Speaker 4 (7:36) I Speaker 5 (7:37) didn't watch rom-com-ish type shows. And my wife said, you got to watch this Insecure. And I'm like, I'm not watching it. And she said, you got to watch it. It's good. And I said, I'm not watching it. And she said, you're going to like it. I said, I'm not going to like it. She made me watch the first two episodes back to back because she was like on episode four. I watched the first one. I was like, all right, it's not bad. I watched the second one. And then I watched the third and the fourth because I was only going to watch the first two. Speaker 1 (8:14) And Speaker 5 (8:15) I just fell in love with this actress who then I had to do a little research and I found out she was a writer and she was. Now getting into the restaurant business and just an entrepreneur and a community folk, you know? Speaker 4 (8:32) Yeah. Kind of like Speaker 5 (8:33) y'all. Yeah. Just in the community doing stuff for Black folks. Giving it Speaker 4 (8:37) back. Speaker 5 (8:38) Giving it back and just so supremely talented. Let's bring on Issa Rae. Issa. Watch him. Speaker 4 (8:46) Watch him. I'm just meeting her for the first time. Speaker 5 (8:50) I'm happy to have you here. Speaker 5 (8:55) She'll be okay. Speaker 3 (8:57) Well, welcome Speaker 4 (8:57) to the table. Thank Speaker 3 (8:59) you so much. I was just nodding and mm-hmm back there. I had so many times I wanted to jump in. Speaker 4 (9:04) Well, Speaker 3 (9:06) what's been going on? How are you? Oh, so much. I'm doing really well. I'm out here still just writing. You mentioned a restaurant that is called Somerville that's in my neighborhood that I'm really excited about. What made you say, all right, I want to open up a restaurant? Speaker 5 (9:22) Is that a dream or was it just circumstantial? Speaker 3 (9:27) You know, it's twofold. I've always said if I wasn't a writer, I'd be a bartender or a waitress. Yes. Okay, Speaker 2 (9:34) well, Speaker 4 (9:34) there you go. I like the Speaker 3 (9:37) food environment. I love serving. I love hosting. And there is a degree of that. And I love eating out. And so since I was young, I've even... Like doing playdates with my brother, my little brother. Our playdates would be restaurant. Yes, and I would be the bossy restaurant owner. Sounds Speaker 5 (9:58) familiar. And then Speaker 3 (9:59) also, I remember my best friend and I have the same birthday. And it was like the 30-something birthday. You were Capricorn, too. I'm Speaker 2 (10:08) a Speaker 3 (10:08) Capricorn. Like Speaker 2 (10:09) me, Speaker 3 (10:09) 17. Yes, you already know. 12th over here. That's Speaker 4 (10:12) why we bossy. Yeah, I know. I don't like Speaker 3 (10:15) to admit it. I don't want to give my mother that satisfaction. But we were just out. We always celebrate our birthday together. We went to dinner. And we were just like, let's go. Like, we're trying to go out. And in your 30s, you're not trying to go to a club. You're trying to go to a place to lounge and have a good time. It was so hard. To find. So many different spots. And it just wasn't the right vibe. It was just, and it infuriated me. I was like, we are both from LA. We cannot find a spot with us that's just a good time that'll cater to us. And that was like my villain origin story where I was like, I want that in my neighborhood. Speaker 4 (10:52) Man, doing it with your little baby boss self. Speaker 3 (10:55) Were you going to say something? Speaker 4 (10:56) I wanted to find out. Go ahead. We talk about friendships and we will eventually. read a letter from one of our listeners who's seeking advice around friendships. But something people ask me, you know, which applies to you, is that as you've become Issa Rae, you know, how has that affected friendships for you? Or has it, you know, have you become more cautious? Have you... Have people come in and out of your life? Have you thought about it differently or felt like you needed to think about friendships differently given your, you know, your ascent and who you become? I Speaker 3 (11:37) have been very lucky that I've had, you know, friends since high school because I'm from L.A. And there is a sense of this feeling like my job. Like I don't, I didn't move here to. become myself. I was already here and I grew up around this environment and a lot of the people that I went to school with are my friends still. And even my name, my name is Joey Sajope. That's how I grew up. And so even the Issa Rae of it is like, those are people who don't really know me. And the people who are my friends, you know, call me by name or my nickname. And so there's such a distinct separation. Speaker 3 (12:22) But I've definitely had friendship breakups as a result. Some as a result of working together Speaker 1 (12:29) as Speaker 3 (12:30) we both descended. Some as a result of not being able to handle the change in position, the time. Like I have a friend who I thought I was going to be friends with forever. But she went through two major milestones. Speaker 3 (12:49) Kind of traumatic milestones really young. She got married when we were in college and divorced when none of my other friends had experienced those things. And I didn't, as a friend, know how to handle that or have the capacity to handle that. And that was actually strike two, I think, on my part for her. Strike one was her father died when she was in college. And she was the first friend whose Speaker 4 (13:14) parent Speaker 3 (13:15) had passed away. And I felt like I wasn't equipped. To like truly be there for her in the way that she needed me to. And that was around the time when I started like rising in my own career. And I felt like she never took my career seriously or my aspirations seriously. So we fell apart and drifted apart. We tried to come together, but we were just in different places. And that was one of my most painful friendship breakups because it wasn't acknowledged. Speaker 3 (13:51) In that way. Right. But I haven't had any like, you're famous, I'm using you type things. Speaker 5 (13:57) Well, that's a perfect segue for our listener letter. It's somebody who fell out of favor with a friend. So, Natalie, are you ready to read Speaker 2 (14:10) us Speaker 5 (14:10) the letter? Speaker 2 (14:11) Let's do it. All right. Speaker 3 (14:13) Yes. Speaker 2 (14:15) Hi, Michelle and Craig. My name is Eva and I'm 32 years old. In my early 20s, I met my friend Kristen through a male friend of mine who she briefly dated. That relationship did not last, but Kristen and I stayed friends. If I'm being honest, though, my friendship with Kristen felt a little unbalanced from the start. I really like friendships to feel effortless, like both sides naturally want to spend time together, check in, show up for each other. But I noticed right away that Kristen wanted to make plans pretty often. I'm a people pleaser, and I had a hard time saying no to her invites when my schedule was already a little too busy with other friend hangs or dates. And when it came to my dating in particular, she had pretty strong opinions about what I was doing wrong. I am not perfect by any stretch, but I do have strong instincts, and I like to trust my gut rather than take advice like this from friends. Still, over time, I really came to respect Kristen. She's incredibly thoughtful and it's a pretty special thing to have someone so much in your corner. We started to go on day trips together and I genuinely appreciated our quality time together over the years. Recently, though, Kristen lost a close family member. And when I sent a text checking in, I got an unexpected text back saying she wanted to stop communicating with me. She said people who were not nearly as close with her had been a lot more supportive. She felt the imbalance in our friendship and wanted it to be over. Honestly, I did not see this coming. I knew our friendship was complicated, but I felt like I was being myself and it was not enough. Ideally, I wanted to continue our