Your Resident Single Friend: Hallmark Holiday Movie Edition

Regular Island readers may recall that I have a mild obsession with Hallmark holiday movies. It's not unusual during the weeks between Thanksgiving and New Year's for me to watch lots of these movies even if I've seen them before; I even have favorites. Yes, they're formulaic and silly and totally devoid of reality and occasionally so traditional/stereotypical it makes my feminist heart hurt but there's something incredibly comforting about them as well. As I shared back in October, I've recently joined an online dating site and to say that it's been a disappointment would be an understatement. My paid subscription ends on, get this, December 24th. It's as if I've been dropped into the perfect scenario for a new Hallmark holiday movie. Today's post is in the form of a "script" for a new Hallmark movie (or what a short story version would look like if such things existed). Yes, it's cheesy and silly but so are all of their movies so it's perfect. You'll need to use your imagination to fill in some of the details and the montages I've indicated. I haven't figured out how to add a meddling older woman and/or an adorable child (staples of all Hallmark holiday movies) but there's always a way and a second draft.

For your enjoyment: The 12 Online Dates of Christmas

A medley of "rock and roll" versions of Christmas songs play over the opening sequence featuring people out and about in a nondescript city getting ready for Christmas (it could be New York or Chicago or Toronto or Cedar Rapids). Families are shopping, couples are pausing to window shop and drink hot chocolate, little kids look in awe at the decorations and at the idea that Santa will be here soon. Our focus shifts to a woman in her thirties (although she doesn't look it) in a seasonally appropriate green coat, juggling several bags, a cup of coffee, and her purse. She's attempting to find her keys and her phone keeps chirping at her, the sign of incoming emails. She sighs, puts down her bags on a nearby stoop and fishes her phone and keys from her purse. She removes her glove and enters her password to access her phone.

"I need to get those smartphone gloves this year," she thinks to herself as her hand immediately freezes. She's only a few blocks from her apartment but stopped to check her email in case it's from work. If she needed to do something to prep for tomorrow's editorial meeting, she wanted to know before she got home so she could plan out her evening.

There are two emails: one from her mother and one from It'sOnlyADate.com, the online dating site she joined back in October. She scanned the one from her mother quickly; details about the cruise her parents are going on for Christmas and then opened the one from the online dating site. She braced herself for yet another "you're not trying hard enough" email that the site thought were helpful. The email never specifically said "you're not trying hard enough" but it was always implied.

The email began friendly enough:

Happy Holidays Charlotte Adams! We here at It's Only a Date hope that you are enjoying the holiday season and gearing up for one of the busiest times of the dating year. 

"This isn't terrible," Charlotte said to herself. Not important enough to have stopped her walk home but now that she was stopped, she decided to continue on.

As we enter peak dating season, this is a friendly reminder that your subscription will end at midnight on December 24th. To take advantage of all the benefits of  your membership, make sure to visit your payments page and select the option for "autorenewal" so we can ensure no disruption of service. We wouldn't want you to miss out on of the person of your dreams! 

Need help with your profile or communications? Add our personalized profile services to your subscription. For an additional $10 a week one of our dating experts will help you maximize your profile and communications with matches. We'll help you be the best possible online dating you! Contact us today!

Happy Holidays,
The It's Only a Date Team

Charlotte sighed and put her phone back in her purse. Seriously, who writes these emails? She found it both amusing and sad that her subscription was set to expire on Christmas Eve. It was sort of maudlin really and very Hallmark holiday movie. She picked up her bags and resumed her walk home. She would call an emergency meeting with her friends this evening. They were the ones who encouraged her to join the site in the first place, threatening to create a profile for her if she didn't do it herself. She needed their dating expertise; she wasn't going to spend any more money on services from this site.

Cut to: Charlotte and her three friends, Marilyn, Beth, and Rebecca, sitting around the table at a cafe. The women each have a coffee in front of them and are sharing an enormous piece of chocolate chocolate cake. The conversation about the dating site is already in progress.

"Obviously you should just renew your subscription and give it more time. Dating takes time, like looking for a new job. You shift through all the entry level options so you can find the right one." Rebecca took a forkful of cake.

"You're comparing dating to a job search? That just makes this even worse." Charlotte sipped her coffee, an excellent vanilla latte, and gave Rebecca a mildly withering look.

"It's just because both activities take time. You can't expect to find "the one" if you don't really try. And admit it, you haven't really been trying. You just rate people and hope for the best." Rebecca put her fork down and gave her friend an equally withering look.

"Fine. I have not truly done everything I could be doing on the site. Maybe I'm too old fashioned for online dating. I still like the idea of the guy asking the girl out and all. I'm not an instigator." Charlotte replied.

Beth chimed in, "I think you should let your subscription go and move on. I know so many great guys and can set you up." The women laughed; Beth was terrible at matchmaking.

"I'll pass given your less than stellar history with setting people up but thank you for the offer." Charlotte looked at Marilyn for an opinion. "You're being suspiciously quiet this evening."

"I was just thinking of what you should actually do. I think you should use the last couple of weeks of your subscription to the fullest. Ask guys out, reply to their messages or chats or whatever the hell goes on. Go out on at least twelve dates and then let it expire. After that, you can do whatever you want. You'll probably go on some terrible dates but at least you'll have given it a try." Marilyn finished her coffee and checked her watch. "I've got to go. I'm meeting Dan at Crate & Barrel; I'm helping him Christmas shop for his sisters." Marilyn had just gotten engaged and was trying to fit in with her fiance's family. The other women packed up and left too.

Charlotte lingered at the cafe after her friends left. This was one of her favorite places and it was right down the street from her apartment. Owen, the owner and baker, was amazingly talented and didn't mind if she worked on her articles when she needed a break from her apartment. He stopped by her table to check on her.

"Are you still working on the cake?" He brought her another latte too.

"No, but I'll grab a box and take it with me. My friends never do their part when we order cake." She smiled at Owen. "Can I ask you something? I think I need a guy's opinion on something."

"Sure. Always happy to be the "guy opinion" on things." Owen sat down across from Charlotte.

"If you were on an online dating site and a woman asked you out, would you go? Or is that too aggressive?" Charlotte thought she sounded like a moron. She was a smart, adult woman with a great job, nice apartment, and a pleasant life. Why was she so awkward when it came to this sort of thing?

Owen thought about it for a minute, "I think if you're on one of those sites you have the expectation that either participant in the conversation could be the one doing the asking. I don't know why you'd go on a dating site if you didn't expect a woman to ask you out or if you weren't comfortable doing the asking if you're interested or if someone expresses interest in you."

"Thank you. That's what I thought but the confirmation is helpful." Charlotte took a sip of her coffee. "I'm going to try a little experiment and see if you're right."

"Which site are you on? Or aren't you allowed to say?" Owen got up to grab her a to-go box for her cake.

"I don't think it matters. I'm on It's Only a Date. It seemed like the only one that wasn't oddly religious, for hookups only, or about getting married. However, I seem to be failing and only have until Christmas Eve to really use my subscription since that's when it expires. I don't think I'm going to extend it." Charlotte put the cake in the box and started putting on her scarf and coat.

"Well, good luck. I hope you find whoever you're looking for." Owen started clearing the table.

"Thanks for the advice and the coffee. See you tomorrow!" Charlotte left for home.

Owen watched her walk down the street. He always liked Charlotte and decided to do something about it. After closing he created his own profile on It's Only a Date. Maybe he'd be one of Charlotte's twelve dates of Christmas.

Imagine a montage sequence of Charlotte diving into her online dating account and going on the first six dates.

Seven days later: The women are sitting around the same table having coffee and discussing Charlotte's progress. This time Charlotte wouldn't allow them to share cake since they always left her with the leftovers. She was enjoying Owen's famous pecan pie. Since the last meeting, Charlotte had been on six dates and had six more scheduled before Christmas Eve. 

"So you've just been accepting whoever asks you out?" Beth still didn't approve of Charlotte's plan to date as many people in the remaining days of her online dating subscription.

"Yes and no. In some cases I ask them out if there's something about their profile I like. I've given them all nicknames." Charlotte finished her pie and smiled.

"And the nicknames are?" Marilyn thought this was all hilarious.

"Date 1: Possibly Has a Secret Family Guy because he has all these photos with women and children in them but doesn't explain who the women and children are so I assume he has a secret family." Her friends laughed. "Date 2: Rugby Guy which was confusing because all of his profile pictures were of him playing lacrosse. Date 3: Awkward Screen Name Guy - seriously used "yolo" in a sentence four times on our date. Date 4: Outdoorsy Guy. We met up for a hike and I thought I was going to die. Date 5: Acquaintance Guy - he's from one of the company's we use at work for online editing software. It was weird since we know each other but don't. And Date 6: Weird Dog Email Guy. He wrote me an email about his dog and then spent the entire dinner talking about his dog. She's a Springer Spaniel named Daisy. At least he didn't bring Daisy with him." Charlotte sipped her coffee while her friends considered her list. Owen waved from the counter. She had brought Possibly Secret Family Guy here and the ridiculousness of the date had made Owen laugh.

"Any promising options for second dates?" Rebecca asked.

"Acquaintance Guy has texted and it wouldn't be terrible. The others are all nos for me. I have six more dates lined up. Want to hear their nicknames?" Charlotte shared the next six names: Date 7: Decoupage Guy (apparently he enjoyed decoupage or sarcasm, Charlotte wasn't sure which); Date 8: Very Into Christmas Guy (they were going to a tree lighting ceremony); Date 9: Hates His Family Guy; Date 10: In Need of Some Grammar Lessons Guy (Charlotte should have turned him down but he was very nice online); Date 11: Marathon Guy (no running would be involved in the date thankfully); and Date 12: Awesome Profile Guy (no photo but his profile was the best she had read).

"Are you concerned that Awesome Profile Guy will be horrifying to look at? I think it's weird that he didn't put up a photo. How hard is it these days to take a picture?" Beth was trying hard to find a flaw in Charlotte's plan.

"It absolutely does not bother me. I'll take no photo over awkward selfie on a bed or weird photo of you on vacation with your bros. It might be better since I'll have no preset notions about him being my "type" which I don't believe I have anyway. His profile was funny, seemed completely truthful, and sincere. I'm holding out hope for Awesome Profile Guy."

"Did you ask him out or did he ask you?" Marilyn finished her coffee and was trying to decide if she wanted a refill.

"We asked each other out although I will give him credit for the date since he picked where we're meeting. I'm going to get a refill. Anyone else?" Marilyn nodded and Charlotte took their cups up to the counter.

Beth spoke in a stage whisper, "I think we should do some spying for these last dates. I don't like this idea but I think we should help."

"Or meddle but help sounds nicer." Marilyn didn't disagree. "We can rotate since I don't think I can spare six nights with all the holiday prep and parties I have to go to. Being engaged at Christmas is the worst by the way. Why didn't either of you tell me that?"

Rebecca ignored the question, "Plan of attack: we'll each take three dates. She'll tell us where they're at and then we can share notes over text and email and intervene if we feel it's necessary."

"Sounds like a plan to me. She's coming back." Marilyn changed the subject back to the upcoming dates. "So where are the remaining dates?"

They spent the rest of their coffee date talking about Charlotte's upcoming dates and everyone's holiday plans. None of them noticed Owen inch closer to their table. He was eavesdropping a bit, getting hints at what Charlotte did and didn't like about her previous six dates and her thoughts on the next six. He wanted whatever information he thought would help. He rather liked his nickname, Awesome Profile Guy.

Several days later, December 24th: Charlotte is in her apartment getting ready for Date 12: Awesome Profile Guy. The pile of discarded clothes has grown over the course of the late afternoon; she's been trying on every outfit in her closet for her date. Nothing seems to be quite right; she refused to buy anything new but is now regretting her choice. Her cat, Cheese, is watching her with feigned interest. Finally she comes up with a winning combination: black skirt, grey sweater with an incredibly flattering neckline, purple tights, boots, and a necklace she found at a vintage store. She feels comfortable and attractive. The final five dates were exactly as she thought they would be: fun, a little awkward, but not worth a second date. Acquaintance Guy never got back to her so Awesome Profile Guy was it. If this didn't work out, she would enjoy her single life and never try online dating again. And maybe get another cat. Her phone rings.

"Hey Marilyn. I'm just getting ready to leave. What's up?" Charlotte had met with her friends once more since starting the second half of her dates. Oddly they were all in agreement with her on each date, even Beth. She suspected they were up to something but didn't know what.

"Just wanted to wish you luck. Where are you going again?"

"We're meeting at the Holiday Market on Main and 14th Street. I'm supposed to meet him by the hot chocolate stand on the 14th Street side of the market. We're going to explore the market and then have dinner somewhere nearby." Charlotte applied some lipstick and threw it in her purse.

"Since you don't know what he looks like, how will you know it's him?" Awesome Profile Guy was technically on Marilyn's list but all three women were going on this one.

"He told me he'd be wearing a Star Wars holiday themed scarf and would have hot chocolates ready for us. He knows what I look like so it'll be fine. I have to go or I'll be late. I'll call you later." They said their goodbyes and Charlotte put her phone in her purse. "Cheese, wish me luck." The cat mewed at her and went back to napping. "Good enough."

Charlotte walked to the market at a quick pace. It wasn't far from her apartment and she didn't mind the cold. She was more excited for this date than any of the other eleven; something about Awesome Profile Guy made her happy. She thought this was a very good sign. The market was crowded more than she expected given that it was Christmas Eve; people were packed around the stalls and the food trucks. The ice skating rink was in the middle of the market and it was full too. Charlotte made her way through the crowds and to the hot chocolate stand on 14th Street. As she was approaching, she could have sworn she saw her friends ducking behind a vendor selling knitwear but she couldn't be sure. Marilyn always wore this very specific red coat and that was what caught Charlotte's eye. She shrugged it off as pre-date nerves and continued to the stand. It wasn't as crowded as the other parts of the market and even had a little sit down area with picnic tables. She didn't see a guy wearing a Star Wars holiday scarf. Was she early? No, right on time. She looked around a bit more, going around to the other side of the stand in case he was over there instead. No Star Wars scarf. She waited a few minutes, watching families and couples walk by. No single guys in Stars Wars scarves. She started to walk back around to the other side."He'll be here," she said to herself.

As she turned to go back she saw two things at once: Owen walking towards her wearing a Star Wars holiday scarf (Wookies in Santa hats and what looked like Yoda as an elf; she couldn't be sure) carrying two cups and Marilyn's distinct red coat. She wasn't sure which image was more surprising. She opted to ignore her friends; she could clearly see all three of them hiding/not hiding behind a neighboring food truck and focused on the person she'd been calling Awesome Profile Guy.

"Hot chocolate?" He asked.

"Don't mind if I do. So, you're my date?" Charlotte took the cup from him and waited for an answer.

Owen smiled. "I figured why not? We've always gotten along well in the two years you've come into the cafe so I thought I'd give it a try."

"You could have just asked me out without having to go through the hassle of the website." Charlotte sipped her hot chocolate.

"Yes, but then I wouldn't have gotten an awesome nickname. The nickname makes the online profile worth it. Would you like to walk around or sit?"

"Walk. We have an audience." She gestured towards the food truck and her friends. "They mean well but are a bit overprotective. I have a feeling they've been following me all week. Also, sorry about the nickname thing. You probably heard us talking about you and the other dates." Charlotte was trying to remember if she or her friends had said anything really embarrassing. "I'm sorry if we said anything super embarrassing."

Owen laughed, "I'd probably do the same thing with nicknames. Actually I refer to you as "Writer Girl" to my friends. Done it for years. And that was more embarrassing of an admission than anything you said to your friends."

"That makes me feel better, I think." They walked closer to the skating rink. "Do you always go on dates on Christmas Eve? I'm usually not here but my parents went on a cruise this year." Charlotte was spending Christmas day with her friends and their families.

"I don't date much and have never been out on a date on Christmas Eve. You said your subscription was ending today so I went with it. It's kind of perfect don't you think?" They stopped just short of the ice skating rink entrance. It really was lovely; sparkly and bright. It was exactly like the end of all the holiday rom-coms she watched incessantly in the lead up to Christmas.

"It's like a holiday card. In a good way. Let's sit over there and watch the skaters; I'm terrible at skating or I'd suggest we give a whirl." Charlotte led the way to an empty bench.

"I can't skate to save my life. I'd probably break something." They drank their hot chocolate and began a running commentary on the skaters. Their conversation eventually veered into more first date type topics. Charlotte noticed her friends only one more time, exiting the market quickly waving at her as they did. She took it as a good sign that they were leaving; it meant they approved or at least were going to leave her alone on this one. It was getting colder and the pair decided to go to dinner. Most places were closed because of the holidays but they eventually found a 24 hour diner that was open and not too crowded. They ordered coffees and breakfast for dinner and spent the rest of the night talking and not paying attention to the time. Charlotte finally realized it was almost midnight.

"We should probably go. Our waitress looks unhappy with our presence despite our additional purchases of apple pie and french fries. That should have been a gross combination but it was surprisingly good." Charlotte smiled at Owen.

"It's not like we ate the pie with french fries on top. They were adjacent items. I see your point on the combination and our waitress. We should go." Owen paid the bill, leaving an excellent tip. They waved at the waitress as they exited. She did not wave back.

It was snowing lightly as they exited the diner. "Do you want to walk or get a cab?" Owen asked.

"Walk. Walking in the snow seems like a very Christmas Eve thing to do" Charlotte replied.

"Okay but remember that statement in a few minutes when the snow picks up and we're both miserable." He took her hand and they walked towards her apartment.

"It's not going to get worse." Charlotte was convinced, although she did not share it with Owen, that there was some sort of Christmas magic working this evening. It had been a perfect evening, after she'd gotten over the shock of date twelve being Owen. They'd known each other for years; it just seemed right. The snow did not get worse but they were at her apartment building much too quickly.

"Here we are," Charlotte stopped in front of her building. "I had a really great time tonight. It was unexpected but I'm glad you're Awesome Profile Guy."

"Good. This would have been a terrible idea if you ended up hating me or something." Owen smiled at her, the same warm smile that had been greeting her for years.

"Well, I'd like to go out again if you're game."

"I think that's a great idea. I'm guessing tomorrow is out of the question with it being Christmas and all. How about the next day?"

"What no three day rule? I'm kidding of course. Yes, the 26th would be great."

"Then it's a date. Merry Christmas, Charlotte."

"Merry Christmas, Owen." As they kissed for the first time, the snow picked up dramatically.

"I told you it would get worse." Owen teased.

"Or better." Charlotte kissed him again as the snow whirled around them.

The snow whirls and swirls around the pair as Christmas music plays. We follow a swirl of snow up into the sky. End Hallmark Christmas movie.