The working title of this movie is The Dating Coach, and I’m not sure which title is more boring than the other. Which, as it turns out, is totally apt for this snoozefest.
Twenty years ago, we meet a nerd named Harold (of course). He’s getting spiffy for the freshmen homecoming dance. Is that a thing? I’m Canadian, so there was no such thing of having grade-specific dances. Harold has apparently invited a girl named Annie to the dance. But when she shows up, she’s dressed in a SWEATER (he’s in a cheap suit) and mentions that they’ll meet up with all her friends. Group date! Harold is devastated.
Present day. Harold is still a nerd, but a successful one: he’s an accountant who works from home, and secretly does great landscape photography. His clients, Claire and Steve, are also his friends, so Claire invites him to their daughter Megan’s 9th birthday party. Claire is Annie’s sister, and intones to Harold that Annie will also be at the party. He hasn’t seen her since high school!
Exposition time. Harold and his friend Willie are at a coffee shop, talkin’ about life and women as you do, when a pretty female walks in and smiles at Harold. Willie encourages him to make a move, but Harold’s too shy to approach her. Harold explains to him (and us) that nothing works for him: Internet dating, matchmaking services, blind dates, etc. Willie suggests working with a dating coach. Harold is dubious, but seems to realize he’s out of options.
The dating coach he meets is perfectly forgettable. All I do remember is that her office was decorated like she celebrates Valentine’s Day every day. She just wants his money. Harold would be outraged by the costs, but he never shows emotion, so he’s just neutrally disinterested.
Harold and Annie catch up at Megan’s birthday party. Well, sort of. She barely knows who he is and remembers nothing of the group date that has traumatized Harold all these years. She tells him she’s a event/party planner and that she actually threw together little Megan’s birthday party. He’s impressed even though she literally just threw balloons and streamers around the room.
After the party, Annie and Claire are cleaning up and chatting. Claire mentions Harold in a hinting tone, and Annie’s like “yeah, he’s nice but blah.” We find out that Annie is a player and has dated a LOT of dudes. Also, she’s not really a party planner because she doesn’t actually have a job, she’s just been looking for one. She has been living with Claire and Steve for the past four months while job hunting. Claire is at her breaking point with this and is like, so can you find a day job in the meantime? Annie is stunned by this concept. A day job to cover my room and board while I look for a full-time career???
Jobs are a dime a dozen in Hallmarkland, and she finds a serving gig at some local restaurant right away. She works with a kooky server named Kim (played by the fabulous Kathy Najimy, who, I just found out, is married IRL to the guy that sang Total Eclipse of the Heart in Old School). It’s Annie’s first day and who happens to show up but good ol’ Harold, who’s a regular. Aw.
Even though she lives rent-free in a nice big house and just found a job by basically snapping her fingers, Annie loudly complains in front of Harold and her other patrons about how her car broke down, she has no ride, everything sucks, etc. Fire her! Instead, Harold timidly offers to take her home. Annie is a shameless mooch, so she accepts. On the ride home, she asks why he’s still single (even though she just called him “blah” to Claire), and he explains again that he’s a lost cause and almost got himself a dating coach.
When Annie gets home, Claire gives her a tough love speech; she feels that she’s enabling Annie by letting her stay with them, so she asks Annie to leave and find her own place. This is a rude awakening for Annie, but she says she’ll be out as soon as she gets the money. This is 100% reasonable of Claire and Steve, by the way, but this movie kind of paints Claire in a dick light for it.
Back at the restaurant, Annie tells Kim what’s happened. She’s horrified at the notion that in order to find an apartment, she’ll have to get another job. And work like a normal person?! Doesn’t Claire know Annie has a party to plan?! A pity party for herself, that is.
She mopes around work until an idea comes to her: Harold is single and clueless! She should be his dating coach, even though she hasn’t had a long-term relationship in a long, long time.
In order to do this right, she does “research.” This is not the right word for what she does, because we only see her sprawl out in a really grandiose and cozy library (I legitimately didn’t know if it was Claire and Steve’s personal library, or a weird public one, because it looks nothing like one I’ve ever seen) and read books on true love.
Now that she’s an expert on love, she shows up at Harold’s home office to solicit her dating coach services. Her offer is for eight dating lessons, which she bullies poor Harold into accepting.
Lesson 1: Self-Confidence
Annie arrives for their first lesson and fawns over his record collection of old love songs. She tells him that the most important thing of all is to be confident with himself, so in order to beat him down first, she has him stand in front of a mirror and say his best qualities out loud. But when we switch to his perspective, we see that Harold is seeing his nerdy high school reflected. Aw, you guys, that’s legitimately kind of sad. In one of her first super oblivious moments, she’s amazed that he is still traumatized by his past. To remedy this, she makes him recite aloud that he looks good, while still looking at himself. Annie tells him that he needs more sessions (great, just what every self-conscious person wants to hear!) but they’ll be for free. THE GENEROSITY.
This movie is basically a series of montages/lessons tied together with short scenes, so let’s just skim over what happens: They work out together for his extra credit, Annie tells Kim that it’s exhausting to get him up to speed (nice), Kim tells her that he’s a good tipper and his hair smells like detergent (that’s…not a good thing though?), Harold gets a haircut and gets new clothes and switches to contacts (nooooo, stop inferring that glasses are uncool!). He’s getting confident! Willie can’t believe the transformation, but finds it weird that his high school crush is his dating coach, even though she’s an alleged party planner. Willie: asking all the right questions.
Lesson 2: Breaking the Ice
Annie takes Harold to a fancy bar for the next lesson. She asks if there’s anyone he’s interested in, and he confesses that he thinks the coffee shop girl is cute. Annie tells him that he should approach her next time, but to be himself and not use cheesy pick-up lines. Thanks for this super exclusive advice that the Internet definitely hasn’t offered already, Annie.
She forces him to say hi to a girl waiting at the bar. He actually starts out well in his introduction, but then loses his confidence and shuts down, eventually just walking away without saying anything else. Annie’s got her work cut out for her!
For some stupid reason, Claire is starting to feel bad that she’s asked Annie to leave.
So, Annie and Willie are with Harold at the coffee shop when his crush shows up. Annie basically pushes him toward her. We find out her name is Julie, and she notices AND loves his makeover. They banter about coffee, and she asks him out! Also, Willie is wearing a Bluetooth headset for this entire scene, but it’s never explained why.
Lesson 3: The Art of Conversation
Annie wants Harold to take Julie out for drinks. He admits that his weak point is conversation (dude…), but she assures him to simply ask a lot of questions and listen to what his date is saying. But not too many questions or you come off as creepy!
Later, they role-play with Kim as Julie, while Annie watches and coaches. We do find out that Kim collects animal teeth, makes pie filling art, has pet iguanas, and does jousting for fun. Um, why isn’t this movie about Kim?!
On the real date, Harold discovers that Julie is a real estate sales rep who loves travelling and horror films. She asks if he likes scary movies, and he’s like, yeah sure…but when she invites him to a monster flick, he seems wicked nervous.
Lesson 4: Start Sharing
Harold confesses to Annie that he’s afraid of boring the shit out of Julie when he talks about himself. Annie disagrees with this, even though she knows maybe five things about him by now. Which is a perfect time for him to show her his photography; she’s impressed and says, “You just keep getting more and more interesting.” Not to us, Annie!
It’s been an hour and nothing has happened.
He cooks her dinner and she loves it, since she had no idea he was such a good cook. When he tells her his favourite movie is Casablanca (it would be), she realizes he’s an old-fashioned romantic, which women will eat up.
Julie and Harold go see that monster movie. Despite the fact that he kept his eyes shut during the whole thing, she still likes him and kisses his cheek goodnight.
Riding the high, he goes to celebrate by seeing Annie at the restaurant to tell her she was right about everything, and now everything’s changing because of her lessons!
Willie and Harold go for a jog. Harold thinks he should cook a candlelight dinner for Julie. Willie barely recognizes this new Harold. Meanwhile, Annie confides in Kim that Harold’s demeanour is changing a lot, and that she’s never seen him like that (even though she hasn’t seen him in 10+ years…). She’s worried that he no longer needs her services. Kim suspects she just wants hunky Harold for herself.
Lesson 5: Make Her Feel Special
Annie suggests Harold does something small for Julie to show her he cares. His idea is to take her somewhere in the city that she’d love. Annie’s like, in order to give you a good restaurant recommendation, I’ll need to go see for myself, so maybe we should scout out a place together? Subtle.
They’re now on their dinner in the city, and dressed to the nines for it. He gives her the final payment for her services, even though they are only halfway through? She’s trying to reminisce about homecoming, but she remembers NOTHING about the evening, so she just asks him if they danced together. He says no, and she’s surprised (really though).
HOMECOMING FLASHBACK: Harold’s wearing his little suit and literally nobody else is dressed up. Just as Harold’s worked up the nerve to ask Annie to dance, some jock dude named Matt Schneider cuts in and asks her. LOL, that’s not really the trauma that I was expecting.
Annie’s shocked that that memory has stuck with him that long. She asks if she made him feel that way. Look, I find the idea of a “friend zone” super gross and entitled, and I definitely don’t begrudge a teenage girl for being oblivious to a boy’s crush on her. My issue is the cutesy-naive act that adult Annie seems to pull throughout these dumb lessons, and it just smells all too much like fishing for compliments and boosting her low self-esteem. Yes, it feels nice to know that someone liked you.. But knowing it’s still a source of pain for that person, it’s just all a little icky dipping back into that pool to ask for more details.
Anyway, she does apologize for being 15 and clueless, and then assures him his life is way better than hers now. He’s like, “C’mon, Annie. You’re the prettiest girl from our high school,” and she does that coy, oh-if-you-say-so blushing rose routine, and I hate everything. He’s confident that she’ll get a job and meet someone, but that she just has to Believe in herself, because he does! Who’s the dating coach now? She hears some old love song, and admits she thinks it’d be a good song to have as “their” song, with her future husband. I mean, that’s not something you plan.
When she comes home late from their date – oh I’m sorry LESSON – Claire is waiting up for her. They have a stupid sister talk, reconcile and whatever who cares we’re almost at the end.
Lesson 6: Getting Close
Annie shows up at Harold’s. He’s wearing a deep V sweater with no T-shirt underneath, which is upsetting. He shows her his new nature photos, and she exclaims that they belong in a museum, even though your homebody grandpa probably takes the same quality of pictures as Harold.
This lesson is all about making the first move and getting to first base. She wants to go through a “test run” in which she’ll be the recipient of the kiss AND the coach. Conflict of interest! After they kiss, she thinks it was great and he thinks it was just okay, which is hilarious. Annie insists they should run through it a few more times, just so he’s comfortable when it comes time for him to make a move on Julie. This is all so gross.
Wait, I’m now left to believe that Harold is a virgin, because there’s no way a grown man has to be taught how to kiss a woman on a date if he’s not still a V.
On his date with Julie, he’s taken her to that restaurant in the city. She’s disappointed that they aren’t taking advantage of being in the city by going to see a show, or going dancing in a club. But he makes it up to her by offering to cook her dinner for the next date, and then they make out in the restaurant.
At work, Annie confesses to Kim that she is discovering all these amazing things about Harold when she always saw him as a nobody (lol). Kim’s like, hello you’re an idiot you have the hots for the big H. Annie doesn’t think she can compare to Julie though.
Harold is cooking for Julie, when she, apropos of nothing, asks if he knows of an event planner for some big fundraiser. He does! She also wants to know what their plans are for that evening, since he mentioned dancing, but what he meant was staying in and dancing to his old records. She’s not into it, and Harold is disappointed.
Lesson 7: Compromise
Harold is with Annie and Megan in the park. Annie is excited to tell him she got the job! When she asks how the last date went, he explains that Julie wanted to do something “fast and furious” (eww). Annie tells him that it’s a good thing for them to see one another’s differences and then compromise. She thinks he should invite Julie to do something he really wants to do.
He invites Annie to go take some nature shots by the lake at dawn the next day. In reality though, it’s more like 8 a.m. because the sun is fully up and shining once they get there. Nothing really happens, except we find out the fundraiser is for a park preservation society thing, and she would love to showcase his nature photos for the event.
Later as they go through his prints, he decides to put on a record and dances with her. He ruins the moment by saying Matt Schneider’s not there to steal her away. Let it go, dude! She asks, in this weird dreamy way like she’s fantasizing about it now, if he kissed her goodbye after the dance. He’s like, umm no I waved at you from the car when my mom dropped you off and then we never spoke again. Classic.
Lesson 8: Follow Your Heart
We’re almost done!
Annie comes over to celebrate his “graduation” from her lessons. “It’s official, you’re a heartthrob.” They toast one another and he says he gets to hang out with the prettiest girl from high school, whom he always had a crush on. She asks in disbelief, “You did?”
On his next date with Julie, he takes her outdoors to take photos. She hates everything, ruins her shoes, then gets impatient and asks if he’s done even though THEY JUST ARRIVED! They are not MFEO (See: Sleepless in Seattle).
OMG, this scene. Harold arrives at the restaurant just in time to see a dude joking around with Kim and Annie. It’s Matt Schneider!!! He instantly gets jealous, and when he finally comes in, he acts weird around Annie. She tells him she found an apartment in the city and will be moving in right away. He’s like, great, all your dreams are coming true.
Sweet closure comes in two forms: Claire and Annie have one final reconciliation and hash out their stupid issues, AND Julie breaks up with Harold in a super fake cafe set. He wanted to break up with her too!
So, it’s the night of the fundraiser. Annie’s setting up her shitty party when some old guy comes up all, ARE YOU THE ONE RESPONSIBLE FOR ALL OF THIS? He loves it and hires her for his next company event! He also thinks the mysterious nature photographer is a True Artist.
Ugh. Harold shows up at Claire’s. Claire encourages him to go to the fundraiser. He says there’s only so many times he can let himself be rejected by Annie (dude, it happened just once), because “Matt Schneider really likes Annie, and she seems to like him too.”
YOU LITERALLY SAW THEM JUST TALKING ONCE THROUGH A WINDOW.
Claire basically calls him an idiot, tells him that Annie likes him, and pushes him out the door.
At the fundraiser, the old guy tries to introduce the photographer to the audience. Why? Nobody knows him, he just donated his pictures. UGH!!! Harold shows up just in time, and then gets a speech for some reason?!
He wastes his speech by getting really weird and personal about Annie, who’s basically crying in the audience and not professionally embarrassed at all. He then somehow cues up Their Song?! and then makes her dance with him in front of all these strangers. This is so inappropriate! Everyone starts dancing and it’s all terrible.
Not that I’m upset, but there are zero puns about coaching at the end and that’s just a little disappointing.
Sooooooooo boring. I also have a slight issue with the fact that Annie has kind of consciously/subconsciously been grooming Harold, in a way, to be a good boyfriend for her.
Top IMDb Comment:
So what you learn from this movie is sometimes overtime even though it wasn’t meant to be you can fall in love with that person overtime for real.