Maggie McMuffin shares a movie date memory from her history of queerness and analyzes sex worker representation in the Debra Messing film The Wedding Date.

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Yes, I watched Will & Grace as a high schooler. I was an awkward redhead with a gay best frenemy. Of course, I have since learned that if you are going to be anyone on that show you are going to be Jack and Karen but at the time I thought Debra Messing was more my speed. This, combined with my love of rom-coms set in England, led to me being interested in seeingThe Wedding Date when I was 14 or 15 years old. I went and saw it with my mom and liked it enough to see it a second time when the opportunity arose.

And what an opportunity.

My aforementioned gay best frenemy (now just a friend), Brian, was going on his first date with another dude (Brian was way better about coming out early than I was). Clearly a big deal that was complicated by us living in a conservative town with a naval base. On that base was a theater, that theater was playing The Wedding Date, and our two young homosexuals didn’t feel they could go alone.

So Brian brought me, and his date brought a lady friend. The boys sat in the middle and we sat on the outside. Boys paid for the date and got to hold hands the whole time while seemingly on a double date with two girls. (In retrospect, I’m pretty sure that other woman was also not straight.)

When I told my dad about this his response was “You managed to get a guy to pay for a date that you would never have to put out for? Good job!”

So while I don’t remember a ton about this movie (but still a decent amount. Certainly more than some of the other films I’ve re-viewed), it has a special place in my heart and my history of queerness and, in a weird way, my eventual entry into sex work.

At the time I didn’t know all that though. It was just a funny story that featured some bitterness about love (I was all about love-bitterness in high school and still am today!) and awkward people and a British setting. All of that is secondary to my current thoughts of  ‘AND A MALE SEX WORKER WHO CATERS TO WOMEN.’

Seriously. That very rarely happens in pop culture (and life) and I don’t really care about the other stuff in this movie. I mean, maybe it’ll still be funny ten years later or maybe now it’ll piss me off because, barring Tyrion and Shae in Game of Thrones (seasons 1-3 only), I hate stories where a sex worker gets together with a client because even though it sometimes, on occasion, very, very rarely happens, I don’t want there to be movies out there encouraging the idea because, no, the stripper does not want to go on a date with you stop asking for the love of god.

But I doubt this can be as bad as Pretty Woman so let’s go to a wedding!

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We open with a wedding invitation to ‘Kat Ellis and Guest’ which is a quick way to tell us that Kat (Messing) is SINGLE. Also her sister is getting married. The invitation is super boring and basic so they throw some rose petals onto it. This transitions directly into a montage of Male Escorts ads in a black and white classified section. There are a lot of them. And I paused on the first two screens to see what was up and they’re all actually written in a different voice and style. I could not find any jokes hidden in there. Way to go whoever put that together.

The ads must be good because next we get a shot of New York with a voice over by Nick Mercer (Dermot Mulroney), giving a pep talk to Kat about how he’s going to be late to their international flight and she needs to send him his ticket and also she should stop freaking out. But Kat loves freaking out! So we are treated to her packing last-minute for this trip to England, taking a quick break to look at some picture of her and a dude. We also see where she got this idea to hire Nick because the camera pans to a magazine article called “HIRE YOUR DATE. THE NEW WAY TO DATE.” This is important because Kat is going to carry this article around with her for the rest of the film and consult it. A relative will too. Because middle class white people love reading stories about sex workers.

Speaking of, as we learn on the plane (which Kat boards with, like, nine pieces of luggage 15 minutes before takeoff because even though it’s a post 9/11 world she works for Virgin Air and can do that I guess? Could you just put nine pieces of luggage on a plane 10 years ago and not get charged 50 bucks for each one?), Kat and Nick have never met. But she has his full legal name. And the screening process he covers later in the movie is pretty shaky. But sure, he’s just gonna board an international flight with some random woman. I don’t know if male escorts who see women do that or not but if they do I hate them for getting to live in such a safe world. You couldn’t pay me enough to get on a plane with some dude I’ve never met. Hell, even getting sat next to a dude on a plane during a regular flight makes me glare.

Anyway, Kat fills Nick in on her family by telling him that it is not like on sitcoms where ‘everyone is out of their mind but they’re family so at the end of the day you love them.’ Totally not like that. But she has a stepdad and she loves him a lot.

They land and Kat insists that she change because Nick’s tie matches her dress. They change at a pub and she goes through everything. This, and lots of other moments in the first 45 minutes of the film, really serve to highlight how nervous Kat is and Debra Messing plays it off well. This isn’t comically falling over and being an adorable klutz. Messing plays Kat like a woman who is genuinely two seconds away from having a panic attack over anything not being perfect, someone who is deeply worried about what people think of her. Oddly enough, at no point does the film fall into tropes about her job being an issue or how people constantly try to set her up on dates. Rather, as someone who lives an ocean away from the rest of her family and the place she grew up (which seems to be London since it’s an unnamed large English city) they instead make references to her previous engagement that fell apart and to the fact that “she was very popular with the boys in school.”

And since Kat’s ex who dumped her is the best man at this wedding, people are actually pretty understanding of her being nervous at this thing. I mean, it’s super awkward and it gets more awkward as the movie progresses and we learn why he dumped her.

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Anyway, we get to the wedding and meet everyone. Kat’s blunt mother, her adorable and attention grabbing sister Amy (played by Amy Adams pre-leading lady upgrade), her sister’s fiancé Ed (Jack Davenport) who is actually a decent guy, Kat’s stepdad, the ex, Jeffrey, and Kat’s cousin TJ who quickly becomes a slutty comic relief character by entering and making a joke about having multiple gynecologists.

We follow all these people for the weekend. Kat pays Nick in a coat closet at the first event because I guess there wasn’t ever any time on the 16-hour plane ride. They are placed in the same bedroom at her parent’s house which is awkward because Kat finds sex for money “morally repugnant” and totally isn’t doing that except she totally will bang Nick by the end of this movie. Anyway, it’s really bad. Kat asks Nick questions about things he said in the article. Because, surprise! He was the escort they interviewed for the article and Kat’s friend at the magazine told her how to find him! Professionalism! Nick is not impressed and trolls Kat on every question, up to making up a story about his mother being a stripper who was really inappropriate with him. But the real answer is that it’s not about sex and he wants to give people company.

Honestly, with the exception of the eventual romance, Nick isn’t a poorly written sex worker. He gets eyeroll-y at the shit Kat pulls. He’s good at lying and calming Kat down, as well as maneuvering social situations they end up in to make Kat look good in front of her ex. There’s even a thing later on where he tells Kat he hates anchovies and four scenes later he’s eating some that are offered to him so as to fit in more. And then there’s this exchange at the bachelorette party, where all the ladies faun over him.

“Must be great, being paid just for being you.”

“Who says I’m being me?”

By the way, the romance is weeeeiiird. Like, he spends one day with Kat (where he is often annoyed and insulted by her) before the feelings kick in? And then they go to the stag and hen parties. Nick spends time with Jeffrey and learns he’s sad and in love with someone (we are led to believe it is Kat) but also Ed, who he learns has never had a fight with Amy. Ever. Like ever ever. They are the perfect couple.

Meanwhile, Kat gets super wasted with the ladies. Her sister gets all teary and talks about having second thoughts about marriage. “I shouldn’t be allowed to get married,” she cries, and hugs Kat really intensely and keeps repeating she loves her even if they haven’t always gotten along.

I’m sure you can see where that’s going.

Kat stops by an ATM on the way home and bangs Nick in her stepdad’s boat. She does not pay up front. She does not pay at all because she wakes up asking what happened and Nick, ever the gentleman, tells her nothing. (Even though she was super drunk so even if she was the aggressor, he should have said no because consent, dude. If someone who was putting up a pillow wall between you the night before and was afraid of seeing your penis shows up drunk and starts undressing you, you get that bitch some water and put her to bed and not like that.) But then he acts all snippy and find the money but Kat is like ‘What’s the deal, you said nothing happened?’ and also says she didn’t want to seem like she was expecting freebies, which is the first considerate thing she ever says about Nick’s job.  Nick gets upset and says he would have told her if he was going to charge her and nooooooope. Nope. Nope. Debra Messing is cute and all but there’s no way I buy that the escort who has known her for 36 hours is taken enough to just give it to her for free. Especially since he apparently charges $2000 per sexing? Like, no. No.

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But the night does a lot to boost Kat’s confidence. After this she’s visibly surer of herself. And when she is drunk and seducing Nick, she’s genuinely hot. Like, you can see the young heartbreaker Kat was before she got her heartbroken and became self-conscious.

Speaking of getting her heart broken, we learn about that at the rehearsal dinner. After a great dinner where everyone is getting along, Kat’s ex follows her into the wine cellar and starts trying to tell her something. By this point she’s reclaimed her confidence and doesn’t care what he has to say because she’s over him. Then he blurts out that he slept with Amy and Kat goes stone face angry. She walks upstairs and Amy, TJ, and Nick (Amy told Nick all this earlier when he walked in on Jeffrey hounding her about it) immediately know what’s up. Knowing that other people know just makes Kat angry enough to wander off into the nearby village while Ed, still in the dark about the affair, keeps asking what is going on.

We unfortunately have to sit through a scene where a wet Kat and Nick (like there was thunder and we never saw rain but both of them were clearly rained on? I think there might be an MPAA guideline that lovers arguing in England have to be rained on before they can express their feelings) snipe at each other and Kat is like ‘I believed all of this!’ and Nick is like ‘You can’t call me a liar! You dragged me out here to lie to people!’ And Kat tells him:

“I was so desperate for everyone to think I was happy that I paid 6,000 dollars for a lie and at the end of the day the only one who ended up falling for it was me. I wish I could say it was worth it.”

This is all the worse because Nick asked Kat’s dad for permission to date her earlier. Because he’s in love with her now. And it makes no sense but Mulroney actually does play off being hurt well. Hell, even if Nick wasn’t in love with Kat that would be a fucked up thing to say. It’s basically Kat getting mad at him for him being good at his job and her being bad at understanding the boundaries of their arrangement.

They split up and Ed let’s Nick stay in their boat house. Kat goes home and Amy thanks her for not outing her because she wants to tell Ed. She was just waiting for the right moment.

“You should really time it right. So that when you tell him you were repeatedly screwing his best friend he won’t feel like the whole world is collapsing around him and there’s no escape because you tricked him into marrying you.”

Kat is DONE. Kat will do the wedding, she’ll give a speech, and she’ll spend the next day acting like everything is fine and all that happened was that she and Nick got in a fight “but right now, tonight, I’m not gonna pretend it’s okay.”

I’m…I’m kind of amazed. There isn’t a tagged on shot of Kat feeling bad after her sister leaves in tears. And Amy Adams plays Amy like someone who fully understands that what she’s done is wrong. I mean, we’ve spent this whole film watching her express guilt and anxiety over something and now that it’s out in the open Amy is pretty broken. This whole scene is just COLD. Like, even though this a rom-com moments like this are played more like a straight forward drama and when we lead into the wedding prep montage of the next day, we’re shown the awkwardness rather than getting beat over the head with it. Things like Kat and Amy’s mother always being between them and Kat dropping her smile as soon as the photographer exits.

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But someone is gonna get told something and that someone is Ed. Amy comes clean at the church before the ceremony can start and Ed’s response is first sadness and then to go find his best man and chase him down with the full intent to beat the shit out of him.

TJ trips Jeffrey during the initial chase, btw. Because TJ, despite being a minor character, is pretty awesome.

So Ed is chasing Jeffrey and Jeffrey says they slept together before Ed and Kat got together. Ed doesn’t care because it still means Jeffrey cheated on Kat. Ed is a good person.

While this goes down everyone waits at the church. Kat and her stepdad have a heart to heart where he talks about that article because I guess he found it or something. And he gives Kat a really nice pep talk where he doesn’t say he knows how she and Nick met but he totally knows how she and Kat met. And that Kat shouldn’t care what people think because if she loves him and he loves her, then she should be with Nick. And this scene would be great if it made any sense whatsoever for Nick and Kat to be in love. Because it’s someone saying ‘So your loved one is a sex worker and people may give you shit for that. Fuck them. Do what makes you happy.’

Kat agrees and goes to the boat house to find that Nick has left her a letter and a full refund and is going back to New York. Except he totally runs into Ed and Jeffrey on the way there and gives Ed a ride after Jeffrey gets away.

On the way back, Ed upgrades Nick to best man after Nick convinces him to give Amy a second chance. Nick and Kat make up. (“I would rather fight with you than make love with anyone else.” Ew. You were doing so well, movie.) Amy and Ed get married. Kat gives a speech that makes Amy all teary. Because Amy is, at this point, feeling pretty fucking lucky.

There are some words saying what happened after the movie. Amy and Ed have great makeup sex, TJ gets laid, and Nick quits his job (what?) and “took Kat on their first date. Nick paid.” (WHAT?) Oh and Jeffrey is shown working out naked in view of a hot woman because he “learned absolutely nothing.”

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This movie isn’t terrible. And honestly, even though the romance annoys me it unfolded in such a way that I’m not completely pissed off.

What I do wish though is that this rom-com didn’t have that romance but kept the growth Kat achieved with Nick’s help. People do get help from sex workers. People gain confidence from us, whether we’re escorts, strippers, surrogates (how Nick started out), PSO’s, etc. This job is about more than sex. There’s a scene in the film where Nick acts like he’s gonna get sexy but just gives Kat a very blunt pep talk and breaks her shell open just enough that she can pull herself the rest of the way out.

And while it’s good that there was a non-pushy scene where Kat was told it’s okay and not shameful to date sex workers, it does bother me that she ended up with Nick. Sometimes people develop relationships with their preferred sex worker and it can be truly special and meaningful and it does not have to lead to dating. Usually it does not lead to dating because sex workers need to make money. Like, you don’t go out for drinks with your therapist after appointments. So it would have been good to have this movie end with Kat telling Nick thank you for helping her and him affirming that she did a lot of growing that weekend and that he was happy to help. And then Kat could have moved on from Jeffrey and perhaps tried dating again and going back to being her previously fabulous slutty self rather than getting over him by jumping into a relationship with someone else she just met. Especially someone who she doesn’t fully get along with. Yeah, he’s hot. Yeah, he’s nice to her. But there are enough moments in the first half of their weekend where Nick is inwardly reminding himself that he’s getting paid 6,000 dollars to be on this trip.

Also, Nick likes his job. He says he does. More than once. And even though it’s not all about the money, he makes a TON of money. There is no reason for him to quit that job to be with someone who finds that job “morally repugnant” (oh and despite Kat’s growth, she never is shown as getting less judgmental about full service work) and then to fucking pay for the first date. Dude doesn’t have an income anymore and Kat does. Make her keep paying.

But aside from that, I liked the movie. The characters are more than the usual 2D rom-com stock and the cast puts in good performances. The foreshadowing is there but not overwhelming. This isn’t a great movie and its tone is often stuck between being an actual comedy and being a drama which meant I was often letting it drift off into background noise. Like, there are some funny lines, but I have a hard time saying this script is funny enough as a whole to be labeled a comedy. I would say that if you’ve ever got a sick day and want something easy to watch, this might be a good choice.

Though I am wondering if Nick is ever gonna tell Kat that he had sex with her when she was blackout drunk. They don’t include that part in the epilogue.

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