Her Secret Santa

by Kelli Callahan

  Elly: Totally not the direction I was going with it.

  Ian: I know. :)

  Elly: I’m on my way home. If you’re not busy, I might want to hear another joke later…

  Ian: Only if you tell me one first.

  Elly: Deal.

  I wasn’t entirely sure why I kept messaging Ian. Common sense told me to delete the app and move on with my life—the only reason we got matched was because of a system glitch. There was just something about his humor that made me hesitate every time I considered pressing the button that would erase the app from my phone.

  Ian’s one-liners were corny, and his dad-jokes were absurd, but I still liked them. The fact he didn’t immediately end the conversation when I told him a few dirty jokes showed me that he wasn’t completely lost his in G-rated world. I just wasn’t sure if our banter was leading to more—or if I even wanted it to go further than the text messages we were exchanging.

  Am I even relationship material if the right guy does happen to come along?

  I braved the Christmas traffic, paid my Salvation Army tax at the market, and left with enough groceries for the weekend—along with two bottles of wine. I still planned to go into the office, but that didn’t mean I couldn’t enjoy the rest of the time I was going to spend alone in my apartment. Deliveries always took forever on Friday and Saturday night, so it was easier to just make something than stare at my Door Dash app until the driver arrived. It was also a lot less expensive. I changed into my pajamas as soon as I got to my apartment, made my favorite version of pasta-for-one, and sat down on the couch with my phone in my hand.

  I’m kind of excited to message Ian again…

  Elly: I’m ready for that joke now.

  Ian: You’re supposed to tell me one first.

  Elly: It won’t be clean…

  Ian: I didn’t think it would be. It doesn’t even have to be a Christmas joke.

  Elly: Okay, what does it mean if a guy remembers your eye color after your first date?

  Ian: He thinks they’re pretty?

  Elly: No, it means you have small tits.

  Ian: That may be one of the tamer jokes you’ve told me. :)

  Elly: I didn’t want to scare you away before you told me one.

  Ian: Is that the only reason you don’t want to scare me away?

  Elly: Don’t ask me that.

  Ian: Why?

  Elly: Because this is fun.

  Ian: That’s fair. Are you ready for your joke?

  Elly: Yep!

  Ian: What’s the best Christmas present?

  Elly: An expensive one?

  Ian: Nah, a broken drum. You just can’t beat it!

  Elly: Hopefully you buy better gifts for your niece and nephew.

  Ian: Whatever they want, usually.

  Elly: Lucky kids!

  Ian: What do you want for Christmas this year?

  Elly: Nothing.

  Ian: Really?

  Elly: Not getting gifts kind of goes hand-in-hand with not celebrating the holiday.

  Ian: There’s nobody that you want to buy a gift for?

  Elly: No.

  Ian: Not even your family?

  Elly: I’ll buy what is necessary. That doesn’t mean I’m excited about it.

  Ian: Why don’t you like Christmas?

  Elly: It’s complicated. I don’t really want to talk about it…

  Ian: Okay, what do you want to talk about?

  Elly: It’s Friday night. Don’t you have better things to do than talk to me?

  Ian: Not really. Why? Am I keeping you from something?

  Elly: No.

  Ian: Then what do you want to talk about?

  Elly: I got another joke for you.

  Ian: Okay. :)

  Elly: How many sorority girls does it take to change a light bulb?

  Ian: Hmm. I can’t say I’m up to date on my sorority humor.

  Elly: One. She holds it, and the entire world revolves around her.

  Ian: Funny. I take it you’re not in a sorority? :)

  Elly: No, and now that I’m done with college, I don’t even have to put up with them anymore.

  Ian: Oh? You graduated already? Your profile says you’re still a student.

  Elly: It hasn’t been updated in a while. I got a job before graduating that didn’t require me to finish my degree.

  Ian: I guess that explains why you’re always at work.

  Elly: Yep!

  Ian: Ready for another joke?

  Elly: Absolutely!

  Ian and I traded jokes, along with a few tidbits of information about ourselves, for what felt like a couple of hours—but when I looked at the clock, I realized that it was past my normal bedtime—even for a Friday night. I never even poured a second glass of wine. I was scared to admit how much I enjoyed the conversation. He was respectful when I asked him to back away from a subject, but he didn’t seem to mind any of the questions I asked. There was a part of me that was tempted to continue the conversation, but I did want to go into work the next day, so I decided it was time to call it a night.

  Elly: It’s getting late. I have to work tomorrow.

  Ian: On Saturday?

  Elly: I have some stuff I need to catch up on.

  Ian: Okay. Do you want to talk tomorrow night?

  Elly: Maybe…

  Ian: I’ll try to come up with a few more jokes.

  Elly: How about a dirty one?

  Ian: I don’t really have any of those.

  Elly: I bet you can come up with one. I’ll be waiting. :)

  Ian: Fine, but if I tell you a dirty joke, then I want something in return…

  Elly: I reserve the right to say no.

  Ian: It’s nothing bad.

  Elly: Okay, what is it?

  Ian: I want to see a picture of one Christmas decoration at your place…

  Elly: Seriously? Why can’t you let me be a Grinch?

  Ian: It’s up to you. If you want me to tell you a dirty joke, then that’s the price…

  Elly: I’ll think about it. How would I send it to you anyway?

  Ian: There’s a button at the bottom of the chat. All you need to do is click it and take a picture.

  Elly: Okay. I’m not saying I will…

  Ian: Then I guess I won’t have to tell you a dirty joke.

  Elly: It better be a damn good one!

  Ian: Then it better be a really festive decoration!

  Elly: Goodnight, Ian.

  Ian: Goodnight. Sweet dreams…Of sugar plums.

  Elly: Ugh!

  I wasn’t thrilled about having to put up a Christmas decoration, but I was curious to know what kind of dirty joke Ian would come up with. I put my leftover wine in the fridge, cleaned up the kitchen, and walked to the bedroom. I caught a glimpse of myself in the mirror and had to do a double take—I had the silliest little grin on my face, and I didn’t even realize it. Ian definitely knew how to make me smile. It was really easy to talk to him.

  Ian checked so many boxes on my list of qualities I would look for in a guy if I was serious about dating someone. I just wasn’t sure if I could open myself up like that. I certainly didn’t think I could magically transform into someone that was eager to celebrate the holiday season, even if I had someone to share it with that didn’t bring me a lifetime of grief.

  I’ll put up one decoration—just to humor him.

  Chapter Six

  Ian

  I walked upstairs to my room, and I had a feeling in my soul that was different from the loneliness that normally resided there after an evening alone. I didn’t toss or turn when my head hit the pillow. I was relaxed and happy. I slept through the night and woke up feeling so refreshed that I didn’t even realize I hadn’t made a pot of coffee until I had been up for almost an hour. I never thought I would be interested in another woman after my relationship with Abigail ended, especially after so many dates ended in disaster because the memories had a tight grip on my heart—but my interest in Elly seemed to be growing with ev
ery conversation we had.

  I have no idea if this is entirely one-sided, or if she’s still talking to me because she feels some sort of connection too…

  There were things Elly didn’t want to talk about. I did my best to back off when she wasn’t comfortable with discussing certain aspects of her life. I might have been a little pushy when we talked about Christmas, but she hadn’t shut me down entirely—I took it as a sign that maybe she had a little bit of holiday spirit left. It was buried under something that she wasn’t quite ready to share. I wasn’t going to give up on it. I felt like it was a barrier that could be broken down, and possibly even the key to finding out if things could go further than a few jokes that we shared over the app.

  I need to come up with a dirty joke. If she really calls my bluff and puts a Christmas decoration up, then I have to deliver on my promise.

  I wracked my brain throughout the day. She didn’t seem to have any limit to the dirtiness of her jokes, but I still felt like she was just testing me with a few of them. I wasn’t sure if I was ready to joke about jingling Santa’s balls, but I could venture outside of the corny one-liners and dad-jokes that made up my usual repertoire. I came up with a few, and shortly after I finished dinner, my phone lit up with a message from her. I clicked the Secret Santa Romance app and saw that she had shared a picture—it was a Christmas wreath hanging on the wall.

  Elly: There you go. I put something up.

  Ian: It’s a very nice wreath. Good job. :)

  Elly: Don’t get excited. I’m not leaving it up very long.

  Ian: You put it up. That’s a pretty big step. Where did you get it?

  Elly: Someone in my apartment building sells them. I think the money goes to charity…

  Ian: A nice decoration and a little charity—that’s two big steps.

  Elly: I already gave money to the evil Salvation Army Santa too, so I’m all caught up on my charity this season.

  Ian: I suppose that’s one way of looking at it.

  Elly: Okay, I’m ready to hear my dirty joke now! Don’t keep me waiting!

  Ian: Alright. Why is Santa so jolly?

  Elly: Are you stealing my White Christmas joke?

  Ian: No.

  Elly: Okay, why is Santa so jolly?

  Ian: He knows where all the naughty girls live. :)

  Elly: Giving them coal makes him happy? He really is a bastard…

  Ian: It was supposed to be a dirty joke…

  Elly: It’s tame, but I did laugh.

  Ian: Then my debt is paid.

  Elly: I’m not letting you off that easy. I bet you had to come up with a lot of dirty jokes before you settled on that one.

  Ian: Maybe…

  Elly: So, tell me one of the ones that didn’t make the cut.

  Ian: That wasn’t part of the deal.

  Elly: Neither was my holiday charity, but I did it anyway…

  Ian: Okay, fine. What did the gingerbread man say to the vibrator?

  Elly: Hmm. I don’t know.

  Ian: Why are you shaking? I’m the one that’s about to get eaten!

  Elly: That’s a little better.

  Elly seemed pleased with my two dirty jokes, even though I didn’t think they were very good. Thankfully, she didn’t ask for a third one because the list I came up with wasn’t going to get any better. We talked about normal stuff for a little bit—she told me about her job and a project that was stressing her out. I suggested a drink, and she admitted that she was already enjoying a glass of wine. I told her a few more corny jokes when the conversation seemed to be waning, and I realized that I was going to run out of those soon too. If I was going to try and push the conversation further than the screen that separated us, it was only a matter of time before there was no material left to keep the conversation light and jovial.

  Ian: Can I ask you something?

  Elly: Sure!

  Ian: Will you let me be your Secret Santa this Christmas? All you have to do is click the button next to my name and hit accept.

  Elly: I don’t think that’s a good idea…

  Ian: Why?

  Elly: This is fun. If I click that button, it becomes serious.

  Ian: You don’t even have to get me a gift.

  Elly: Why do you want to be my Secret Santa? You don’t even know me…

  Ian: I like talking to you.

  Elly: So, keep talking to me…

  Ian: I’d like to see one of those beautiful smiles you say I bring to your face.

  Elly: Hold on.

  I stared at my screen, waiting to see if Elly was going to hit the accept button. My pulse began to race in my chest, and my heart began to beat a little harder in my chest. I couldn’t remember the last time I had that kind of reaction when waiting to find out if a woman was going to say yes. The screen lit up, and I looked down to see a picture—of Elly. She looked a few years older than she did in her profile picture, and she was even more stunning than I realized. Her misty gray eyes were extremely vibrant, and the smile on her face looked like it could light up an entire room. It looked a lot more genuine than the half-smile she had in her profile picture. Seeing it made my stomach flutter.

  Elly: There. Now you have a picture. It will last a lot longer…

  Ian: You’re beautiful.

  Elly: My phone has a lot of great filters. :)

  Ian: I don’t think a filter made you smile.

  Elly: It’s getting late. I should go to bed.

  Ian: I really can’t convince you to let me be your Secret Santa?

  Elly: No. I just don’t think it’s a good idea.

  Ian: Will you think about it?

  Elly: Thinking about it isn’t going to change my mind.

  Ian: Okay, then I want something else from you the next time we talk.

  Elly: More Christmas decorations?

  Ian: No, I want you to give me three good reasons why you don’t think it is a good idea.

  Elly: I could list them right now…

  Ian: No, I want you to really think about them.

  Elly: Fine, I’ll have them for you tomorrow.

  Ian: Sounds good. Goodnight, sweet dreams.

  Elly: No jokes about sugar plums?

  Ian: Nah, I want you to dream about something better than sugar plums tonight.

  Elly: Goodnight, Ian.

  I took my chance. I wasn’t sure if it was going to blow up in my face, or if she would put some thought into it. She obviously liked talking to me—that seemed like a good foundation for more than a conversation. I just needed to find a way to get Elly to see past her hesitations and convince her that it was a risk worth taking. In order to actually do that, I needed to know what was holding her back. It would have different if we were in the same room and talking face-to-face. I could gauge her reactions and get a feel for them. That was impossible over the phone. I couldn’t even tell if I was chipping away at all of those hesitations. I had to believe I was—because mine had already begun to break down.

  I toned to trust my instincts here. I can’t ignore them.

  I trusted my instincts when they told me that I wasn’t going to find anyone else after Abigail. They caused me to put an abrupt stop to every relationship I attempted after her before any of them even had a chance to get off the ground. I always believed they were sparing me from the eventual heartache of having to tell someone I didn’t feel the same way—it was easier to stop things before they ever got to that point. My instincts—those gut feelings that didn’t always make sense—were what made me choose to launch the Secret Santa Romance app in the first place. They hadn’t failed me yet, and they were telling me that I shouldn’t give up on Elly, even if she had enough hesitations for the both of us.

  I just want to have a chance to keep putting that beautiful smile on her face.

  Chapter Seven

  Elly

  “Why is this so hard?” I stared at the ceiling and sighed.

  I was alone in my bedroom, but I had been talking to the wall for nearly t
hree hours while staring at the blank screen on my phone. I planned to make a list of reasons for Ian as soon as I got up, but it was almost noon, and I didn’t have a single one. I also didn’t make it into the office like I originally planned because I got so distracted with the list I was trying to work on. My reasons were so plentiful the night before, but none of them really made sense. They weren’t reasons—they were excuses—and the morning brought clarity I wasn’t ready to accept.

  I should have just rattled them off last night when I had some alcohol in my system…

  There were plenty of excuses I could write down. I was too busy. I needed to focus on my career. Relationships were complicated. Dating was the first step towards a broken heart. It would have been a lot easier if Ian was just a jerk I could blow off without feeling bad about it, but he wasn’t. He was kind, generous, he made me smile—he made me laugh—and he was hot. Every time I looked at his profile picture, I felt a warmth that reminded me how long it had been since one of my date nights chased away those kinds of desires.

  Now I’m just coming up with reasons why I should consider letting him be my Secret Santa…

  I knew that clicking the button meant more than just exchanging gifts. It was an admission of mutual interest—an open invitation for Ian to pursue me. I didn’t want to lead him in that direction if my heart wasn’t in it. I wasn’t cruel enough to do that to anyone, even the jerks that deserved a little disappointment in their lives. Ian seemed like the kind of guy that deserved the exact opposite.

  This should be easy. Why am I making it so difficult? How is a guy like Ian still single anyway? He can’t be as perfect as he seems. Nobody is…

  My first real exposure to love was watching it unravel when my parents got divorced. I was just getting to the point in my life where I started to understand that there was more to it than having a crush on a boy, I thought was cute. My perspective was tainted by the divorce that shattered my youth. I learned to look for faults in everyone instead of trying to see their good qualities. I was still doing that—but I couldn’t see Ian’s faults because he was on the other side of the screen that separated us.