That Time Jenny Mollen and Jason Biggs Tried to Set Boundaries…

We said no to a favor — and things got awkward

Jenny Mollen
Jan 24 · 18 min read
Jenny Mollen at the Iowa airport… with Jason Biggs and a fan in the background.

For Wake-Up Call’s inaugural Hot Mic op-ed column, writer Jenny Mollen shares how she learned it’s okay to set boundaries when you need them — even if it means potentially looking like a jerk in the process.


I met my friend Craig when we were in school together at UCLA. He was a graduate in the playwriting department and I was an undergrad theater major who auditioned for his thesis, a one act about two imaginary superheroes who come to Iowa. While Captain Blasto Comes to Iowa wasn’t the smash hit we’d all anticipated, opening to luke warm reviews from Craig’s professors who’d hoped for something more heady and less like an episode of Dawson’s Creek, the three weeks we spent rehearsing bonded us for life.

Over the course of our 20-year long friendship Craig has helped me move multiple times. He’s driven me to the airport, picked me up from the airport; introduced me to agents and subsequently helped me write letters when I decided to leave them, introduced me to boyfriends and then subsequently helped me write letters when I decided to leave them. He has been a cheerleader, a confidant, bridesmaid and a champion of every endeavor I’ve ever attempted.

While our lives have taken us in different directions, the trunk of his car is no longer scattered with my old headshots, and I no longer call him at 1 a.m. to talk about whether or not I would look good with bangs, we’ve still managed to maintain a unique bond.

Last January, Craig’s mom Deb, unexpectedly passed away. I found out through his wife, who texted me asking if I’d received Craig’s voicemail from three days prior. Of course I hadn’t listened to Craig’s voicemail. I stopped listening to voicemail around the same time I stopped listening to CDs. Ironically, Craig was the one person in my life who still sent me both.

The last time I’d seen Deb was five years ago, when I shared the story of how I’d dressed up as her for Craig’s birthday/Halloween party. In trying to hilariously describe the situation, I accidentally insulted her by saying that I looked like her… “but like the sexy version”. What I meant to say was that I’d intentionally worn fishnets and a shortened house schmata in an attempt to evoke some sort of weird Oedipal shit for Craig. But my words came out wrong, and trying to explain only made matters worse. I left the encounter hoping that the next time I saw her, all would be forgotten and that we could start anew.

Unfortunately for me and maybe more unfortunately for Deb, there would be no do-overs.

When I finally connected with Craig, he was in Arizona with his father — who’d been on a road trip with his mom when she died. Craig had flown in, in order to help his dad get both the body and the RV back to Iowa. Craig detailed the events of what had happened with a calm, even detachment like a nightly news broadcaster reporting on someone else’s life.

“How are you holding up?” I asked, still guilty that I hadn’t spoken to him sooner.

“I’m okay,” he paused silent, taking a moment to choke back his tears before continuing on.

There were rare instances in the past when I’d heard Craig vulnerable: When his now wife broke up with him, when his now wife agreed to get back together with him and whenever he listened to the song “Kiss Me” from the She’s All That soundtrack. I’d been friends with the guy long enough to have heard him weak, but I’d never heard him serious. Serious was something Craig didn’t do. Even in the most macabre of times Craig would have mustered up enough Craigness to deflect or lighten the mood with an off color joke about how he planned to strap his mother into the passenger seat of the RV Weekend At Bernie’s style in order to avoid the cost of shipping her body home but also to take full advantage of the carpool lane.

“Two birds, one body.” I could almost hear him say.

But he didn’t, so I didn’t. And for perhaps the first time ever in our relationship, we were silent.

It was Friday and the funeral was scheduled to take place the following Monday. Craig in no way expected me to come. Or rather, never thought I would. I’d barely made it to his wedding due to an unexpected traffic jam that caused me to sprint down Michigan Avenue in a cheap pair of heels and burst through the church doors like a belligerent ex-lover. I was a decent friend, or an okay friend, or maybe the worst friend ever, but Craig never faulted me for it. He never gave up on me so I couldn’t give up on him.

“Iowa? It’s fucking freezing in Iowa.” My husband, Jason, exclaimed. “And we have work on Monday.”

“So we’ll go for one night! We can’t not go!” I said, already looking up tickets from JFK. “Craig would do this for me. You know he would!”

“Craig is a different kind of person than you are.”

“You mean a better person?”

“Well… yeah.” Jason shrugged.

“This is exactly why I have to go. I need to prove myself to him… I need to prove myself to Deb.” I said, looking up at the ceiling and taking a moment of silence.

“Are you sure that Deb would even want you at her funeral? What are you gonna wear? Something of hers?” Jason asked.

“That is offensive on so many levels. The woman is deceased and wore an XL.”

“Be honest, which part bothers you more?” he chided.

“Jason!” I looked at him hard. “Are you coming with me or not?”

Jason begrudgingly acquiesced and the next morning we were on a flight to Iowa.


Craig drove an hour in the ice and snow from Iowa Falls down to Des Moines to come meet us at the airport. Though we rented a car, Craig insisted that it was no problem — and perhaps just the excuse he’d been looking for in order to escape the miasma of grief and deli sandwiches hanging over his childhood home.

After catching up over some sub par Tex Mex that Craig barely touched — because he’d recently become manorexic, subsisting solely on grapes, clementine oranges and pickled ginger — I took a moment to bring up Deb and offered our deepest, most earnest condolences.

“You think she died forgiving me for the whole impersonating her bit, right?” I decided that there was no harm in asking.

Craig thought for a moment and was about to respond, when he was interrupted by an urgent text from his cousin, Sherry. Family members had been trickling in from across the country all day and Craig had somehow become their defacto cruise director.

“Ugh, Sherry.” He said, shaking his head distracted. “I can’t believe she is putting this on me right now. She literally just asked me if her husband could hitch a ride back to Des Moines with you guys tomorrow… She doesn’t even know you guys!”

Aside from Sherry’s husband, Jason and I were the only other guests missing the actual memorial service and driving back to Des Moines on Sunday.

Jason kicked me under the table.

“I mean… you know… if he needs…” I started, just as Jason kicked me again. “Ow!” I accidentally blurted out.

“No, I get it.” Craig nodded at Jason. “It’s presumptuous and Sherry is always pulling this kind of shit. She is the kind of person who will come over to your house with her kids and then drop them off for six hours while she and her husband go out for a date night. It’s too much. And you don’t even know Dan. I mean, he’s a good guy, but still…”

“Yeah, I’d love to avoid that if I could.” Jason admitted, plainly.

“You’d actually love him.” Craig said, before excusing himself from the table to go call Sherry. Jason and I looked at each other sweetly, pretending to not be in a fight until Craig was out of earshot.

“Jenny, you know how I get. It’s an hour drive maybe longer depending on weather.”

“So?”

“So that’s an hour stuck in a car with someone we don’t know. What if he’s like a super fan that won’t stop calling me ‘bro’ and just wants to reminisce about how I fucked a pie for the entire ride? What if he wants me to facetime some college buddy of his that I vaguely resemble? Or forces me to take like a zillion unflattering selfies?” Jason was spinning.

“JASON! Nobody cares that you are famous. A woman has died.” I said, like I was a guest star on Suits. “And if this helps Craig — ”

“Dan is a grown adult. He can hire an Uber like anyone else.” Jason insisted.

“You’re not wrong….” I admitted. “It is kind of inappropriate for Sherry to be putting this on Craig two days before his mother’s funeral.

“Kind of inappropriate? It’s morally wrong!” Jason exclaimed.

“I guess it is.” I said, starting to see his point.

When Craig returned, he told us that he had spoken to Sherry and that everything had been handled.

Jason and I smiled, relieved.


After a quick stop at an antique store where Jason unsuccessfully tried to convince me to buy three different vintage marquee signs, we loaded into our spacious minivan and followed Craig’s Prius back to Iowa Falls.

The drive was icy and the sky so grey, it was hard to tell if it was early in the morning or nearly dusk.

Wearing cashmere sweaters and douchey designer sunglasses, we stared out at corn fields on either side of the open highway, bopping our heads and singing along to John Mellencamp, feeling more connected than ever to the plight of the working class man.

“I’m so glad we aren’t driving that dude back to the airport!” I said, turning around and glancing at Jason’s overnight bag flopping around in our cavernous back seat. “It’s so much more fun to just be alone with you.” I smiled.

“Aw,” Jason squeezed my hand. “I agree.”

“Besides, we always say yes to everyone! For everything.” I added, getting peeved thinking of all the narcissists in my life.

“Which is why it was so important we said ‘no.’ Boundaries, baby! We’re growing up.” He smiled proudly.

Feeling self-righteous and proud of ourselves for taking a stand against the tyranny of all self-involved assholes everywhere, Jason and I cranked up the music and sang along at the top of our lungs like the two imaginary superheroes Craig had always envisioned coming to Iowa.

After a mind-numbingly long journey passing pig farms and factories spewing out presumably poisonous fumes, we entered Iowa Falls, a small rural farm town with one main street that looked more like a two dimensional set you’d find on the Universal backlot.

Several blocks later, we arrived. Craig parked in his driveway then got out and waved us in behind him.

Inside, family and friends gathered in the living room. The adults gossiped and reminisced while the kids scrambled up and down the stairs to the basement, playing hide and seek. Eyeing the buffet table in the dining room, Jason made a beeline for what looked like a pound cake covered in chocolate and then re-covered in pound cake.

I walked into the kitchen and found Craig’s dad, Bill — the spitting image of Craig if he’d been left on high in a dryer for two days. Bill was tiny and tan with wire rimmed glasses and a full head of dark hair. He embraced me hard and thanked me for coming.

“It means a lot that you came all this way. Deb would have really appreciated it.” he smiled, adjusting his glasses and wiping tears from his bloodshot eyes. “Did you meet Craig’s cousin Sherry?” he said, clearing his throat and changing the subject. “She lost her voice on the plane ride in…” Bill shook his head, empathetically patting the shoulder of a woman to his right.

Sherry, a blonde haired yuppie in a Moncler puffer and Ugg boots, turned around and looked at me.

“Hi,” she said in a strained whisper rubbing her diamond encrusted nameplate necklace, engraved with the words “World’s greatest mommy”.

“Hi,” I smiled as just Jason bopped back over with a mouth full of cake.

“Baby, this is Sherry.” I said, exaggerating her name and widening my eyes for emphasis.

“Hiiii.” Jason said, picking up my cue. “I’m so sorry for your loss.”

“It’s okay, I’m on cough syrup.” Sherry nodded, touching her throat.

Jason and I exchanged a look.

“I had to fly here alone with two kids and my husband is flying home tomorrow so I’ll be on my own again… I’m going to be in car for two hours driving him down to the airport and back because nobody else is going that way…” she stared at us.

We stared back. “That’s really annoying.” I glanced at Jason.

“Yeah, bummer.” Jason agreed, holding strong.

“Well, it was nice meeting you.” I smiled again, catching a polaroid of Deb taped to the fridge and finding myself wondering if the slouchy knee high boots she had on in the picture were still in her closet.

Later that night, Jason and I drove to the America Inn, an ersatz Bates Motel situated between the highway and an abandoned junkyard.

“Can you believe she told us that she was going to be in the car for two hours tomorrow? That really felt like she was trying to guilt us!” I said, wandering around our “Honeymoon Suite”, a musky corner suite with yellow shag carpeting, a Keurig coffee maker and bathtub with jets in the center of the room.

“Are you kidding? That’s exactly what she was doing! I’m so glad you stayed strong. It’s still shocking to me that she ever asked us.” Jason said, peering out the window at a heap of discarded plastic and metal, no doubt perusing the piles for another marquee sign to try and bring home.

“It’s pretty egregious. At least we won’t have to see them again…” I sighed, getting into bed fully clothed and falling asleep on top of the sweat-stained duvet.


We woke up early the next morning to the sound of a dump truck collecting trash outside.

Thrilled we’d only agreed to stay one night and had a flight in less than four hours, Jason sprung out of bed, brushed his teeth and flung his carryall over his shoulder. “Whelp, It was annoying, we faced some challenges but overall I think we made the right move by coming.”

“We?” I asked, fishing for a little credit.

“Fine, you. You are a good friend, and I think Craig really appreciated the effort.”

“You think so?” I zipped my suitcase and looked up at him.

“I do.” He smiled sweetly.

Jason was in front of me as I wheeled my suitcase down a flight of stairs to the lobby. He checked us out at the front desk while I wandered over to the continental breakfast buffet to load my bag with snacks for the airplane. Sifting through a variety pack of Otis Spunkmeyer muffins, I heard a raspy voice bitching behind me.

I turned slowly to see Sherry. Dan, her husband stood at the other side of the room looking up flights at a large desktop computer under a sign that read, “Internet Café”.

Our eyes locked and I smiled. “Morning… Anyone up for a muffin?” I asked, holding up a banana nut and a blueberry.

“Are you guys heading to the airport right now?” she asked pointedly.

Jason put his head down pretending not to hear as he walked straight past me out to the car.

“I….” I froze, panicked.

“Umm. Yeah. I’m not really sure at the moment… We are actually thinking of staying another night in order to attend the service.” I lied, making a gigantic U-turn with my suitcase around the lobby and heading back towards the stairs.

Sherry looked at me, dubious.

“On second thought, maybe I should go talk this through with Jason,” I said, changing direction and pulling my suitcase back towards the sliding front doors.

As I stepped outside into the cold, I heard Sherry’s voice behind me, presumably talking to Dan.

“They said, no.” she said, seemingly miffed.

Before I could turn around, Jason pulled up in our van.

“What the fuck?” I said, jumping in with my bag as he peeled away.

“What?” he asked innocent, getting on the highway and heading back to Craig’s for a quick goodbye.

“BABY! You fully ignored her and left me standing there to deal. I didn’t know what to say! I was totally busted. It’s so obvious we are going to the airport right now.”

“So?” Jason shrugged.

“So, I wanted it to be less obvious! I thought Craig said that he handled it and that she wasn’t going to bring anything up to us!

“Well clearly this woman has no respect for Craig! Yet another reason I’m glad we aren’t helping her.” Jason said, driving back to Craig’s so we could say goodbye.

“Your cousin just confronted me in the lobby of our motel!” I yelled at Craig as I barged in. “I thought you said that you handled it.”

Craig laughed and shook his head as he peeled what must have been his eighteenth clementine that morning. “I thought I did.” He shrugged.

“Well, what did you tell her?” I asked, watching Craig’s face disappear behind an ever-growing pile of rinds.

“I just told her that I brought the idea up to you guys and that you got awkward so I dropped it.” he said, innocent.

“Craig! That makes it sound like we didn’t want to drive him!” I shrieked, covering my face with my hands. Even with the coffee brewing in the kitchen, Craig’s clementine compulsion was making the entire house smell like a stale vat of spa water and I was getting nauseous.

“Well what am I supposed to say? I can’t think straight! I’m in mourning.” he whined, sucking down more citrus.

“Oh my God, Jason? Are you hearing this?”

“Yeah, it sounds like Craig made us seem like total dicks,” he said, confirming my suspicions.

“How are we the bad guys, here? We were just responding to her inappropriate behavior,” I said, suddenly feeling the need to defend myself.

“It’s all good. Seriously.” Craig giggled. “But you should probably take off if you don’t want to run into them. They’re supposed to stop by before Sherry has to drive Dan to the airport. It’s an hour there and back, you know. ”

“I KNOW!” I assured him.

Craig walked us out to our car and thanked us again for coming. I told him that I loved him and that if his dad died tomorrow not to bother calling. He hugged me and promised that for all future deaths, he would simply send emojis.

Forty-five minutes later, we pulled into the Des Moines airport.

“That was fast!” Jason shrugged, surprised.

Before returning the rental car, we drove slowly past the departure curb looking for signs of Dan. Out of the corner of my eye I saw a man step into the crosswalk and lunged at Jason’s arm.

“What the!? “ Jason shrieked, slamming his brakes.

“Sorry! I thought you were about to run over Dan!” I shook my head, clocking the pedestrian who in no way resembled Dan. “Can you imagine if we told Dan we couldn’t drive him to the airport only to get to the airport and run him over?” I said to Jason.

“I think I’m going to throw up,” he replied, queasy. “This is all too much. Maybe we should have just taken the guy.”

“Well, it’s too late now. We’re here!”

Once we parked, Jason sat in the driver’s seat not budging.

“What are you doing?” I asked, watching as he neurotically scrolled through his phone.

“I’m checking the status of Dan’s flight. It’s on time! He’s flying to Newark; we’re going to JFK. He leaves out of Gate 3A, 15 minutes after us.”

“Great. What gate do we leave out of?”

“3B.” Jason looked at me.

“Okay, if we see him we see him, we see him.” I said as we worked our way in line up to the security checkpoint. “Let’s just own it. We have nothing to be ashamed of! He’s the weirdo who couldn’t get his own Uber, remember? ”

Jason pulled the hood on his sweatshirt over his baseball cap like a turtle retreating into its shell. We decided to move swiftly through the terminal, board the plane early, and get the hell out of Iowa.“

The TSA agent took Jason’s ID then stared at him — and the flicker of recognition turned into excitement. “Oh my god! Dude! Movie star! Famous person right here.” He started pointing and hollering to his co-workers.

“Yo, can you Facetime my boy from school? Everybody tells him that he looks just like you. DUUUUUUUDE!” The agent took his voice up to an octave I’d never heard.

I looked back at the line of disgruntled passengers waiting behind us, certain I’d see Dan. Luckily, he still wasn’t there. “Maybe he didn’t make it.” I thought, feeling my first tinge of guilt. Should we have just driven him? I started to wonder.

After posing for a zillion unflattering selfies, Jason rushed me down a moving sidewalk, getting us to our gate just in time for boarding. A wave of relief washed over me as soon as we got to our seats.

“We made it!” I whispered triumphant, waving as our plane started to pull away from the gate.

Jason and I started giddily high-fiving as our plane pulled out to the runway. “Hell yes! HELL — ” Jason stopped, cut off by an announcement from the cockpit.

“Ladies and gentlemen, this is your captain speaking. I’m afraid we have some bad news… We are experiencing a bit of a technical issue and we are going to need to head back to our gate and deboard the plane. It’s currently looking like it might be a two to three hour delay. All depends on how fast we can find a backup plane. But we will keep you informed. Thank you so much for your understanding.”

“No! No, no, no!” Jason panicked as our plane did a U-turn on the tar-mac taking us straight back to our gate. Our awkward nightmare was coming to life.

“Oh my god, he’s going to be sitting right there, I just know it,” I started to freak out, already brainstorming what I was going to say when I saw him.

After waiting for every other passenger to get off, Jason and I slowly made our way down the jet bridge back into the terminal. When we arrived, Dan’s plane had already boarded.

“That was a close one! Oh my god. Thank god!” I exhaled, looking around at the now empty gate next to us.

Once we were certain that the coast was clear, Jason made his way up to the information desk to inquire about alternate flights out of town.

The boarding agent did some tapping with her fingers on her keyboard, then offered a potential solution.

“Did you check any bags?” she blinked.

“Nope. Not a one!” Jason said, desperate for good news.

“Boarding has already closed but if I can swing it… How do you feel about flying to Newark?”

I looked at Jason, knowing that there was only one right answer and bracing for its consequences.

“Oh god. Oh shit!” I muttered under my breath. “If he’s seated next to us I swear to god…”

Jason shushed me as we made our way down the aisle of Dan’s packed flight to Jersey.

“What’s up buddy?” I suddenly heard him say.

I picked up my head and locked eyes with Dan who was seated next to a window.

He gave a slight nod but didn’t say a word.

“I think he’s mad.” I speculated, once we were sandwiched into our seats near the lavatory.

Exhausted and embarrassed, Jason tuned me out with his headphones and we didn’t see Dan again until we reached Newark.

“This whole day, Iowa, Craig, his fucking eating disorder, his annoying cousin, everything…” Jason bitched as we rode the escalator down to baggage claim. “What the — ” he stopped, staring at his phone then shaking it, confused. “It’s frozen!”

“What’s frozen? The phone?” I asked.

“The Uber app. Try yours.”

I pulled out my phone and tried to log into our shared account but it was frozen on my phone as well. I tried deleting it then reloading it but still nothing was happening.

When we reached the ground level, I looked out at a taxi line that went around the block. Jason threw up his hands in defeat.

Just then, like an apparition, Dan appeared wheeling his bag straight towards us. “Hey again!” he said, almost friendly.

“Hey,” I said, meekly. “Any chance you could give us a ride?”

Jason looked at me nonplussed.

Riding home that night in the back of Dan’s Car, I thought about how justified I’d felt in refusing to help him. In our normal lives, Jason and I are always going out of our way for people, always overextending. Maybe that’s why we got so triggered. We’d said “no” not just because the idea of taking someone with us sounded annoying but also because we never said “no” and it felt good to work out our issues on a stranger. From our point of view, Craig was in a vulnerable state and Sherry wasn’t being considerate, so we took it upon ourselves to teach her a lesson. Maybe we’d taken our roles as superheroes too seriously, maybe there was no real injustice taking place but more a bunch of people in an uncomfortable situation trying to make things work. Hindsight is 20/20.

Dan turned out to be a pretty cool guy with fairly good taste in music. He assured us that there were no hard feelings, even though I’m sure there were a couple. And I managed to salvage what was left of the relationship by blaming the whole thing on Craig.

“Funerals are times when families need to ban together. What kind of an asshole tells his cousin that he won’t help find a ride to the airport after a funeral?”

“Yeah, what a dick.” Jason agreed.

Dan dropped us off in front of our apartment and even helped us with our two tiny bags.

“Thanks so much for the ride. We owe you one.” Jason said, fully aware of the irony.

Dan smiled and extended his hand, “Actually bro, you owe me two.”


Follow Jenny Mollen on Instagram and Twitter, and read more of her work on JennyMollen.com.

This originally appeared in Katie Couric’s Wake-Up Call newsletter. Subscribe here.

Wake-Up Call

Jenny Mollen

Written by

Past that age where guys try to communicate with me through music.

Wake-Up Call

Katie Couric and friends talk career, culture, politics, wellness, love, and money

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade