Wow, it’s been a little while since I’ve written one of these personal stories, huh? They’re not necessarily my favorite posts to write (that’d be the Dear Dating Bitch advice column posts), but I know a lot of you really enjoy them. So, since February 14th is right around the corner, I figured I’d share a personal story about my most awkward Valentine’s Day.

Not bad, necessarily, just… awkward. You’ll see what I mean. Keep reading to find out more!

Personal story about my most awkward valentine's day

*Note: Names have been changed, as always.

The Guy

Sean* and I actually met in high school, but we didn’t start dating until much later. We stayed in touch after graduation and ended up reconnecting unexpectedly during my second year of college. I was still living in St. Louis, but Sean had moved out of state and was in California at the time.

To say that I wasn’t planning on starting up a long-distance romance during my college years is an understatement. I don’t think either of us was really looking for anything, so the fact that we got together was rather surprising.

But we did.

Sean was coming home for the holidays to visit his family. We’d been talking on the phone and texting for a few months, and there was a definite flirtation brewing. So, when he came in town, we went on a date. That was in late December.

Our first date was pretty good. It’s always odd to go out with someone you’ve previously known as a friend. But after the initial awkwardness of the situation faded, it was clear there was a strong attraction between us.

The Relationship

After that initial date, we spent about two weeks together before Sean had to return to California. Despite the fact that it would be a long-distance relationship for the foreseeable future, we decided to give it a shot.

Anyone who’s ever done the long-distance thing will tell you that it’s hard. And our relationship was no exception.

Of course, we spent a lot of time talking on the phone and texting back and forth. We also sent little gifts in the mail. And I will say that there was a lot of emotional intimacy – we did get to know one another really well. But still – there’s a much different dynamic when you’re not physically able to be in each other’s life.

At the time, I was 21 and Sean was 22. So, even though we were in an exclusive relationship, we weren’t necessarily super serious.

Related Read: 6 Unexpected Benefits of a Long Distance Relationship

Our Awkward Valentine’s Day

Shortly before Valentine’s Day, Sean called to say he was going to be able to fly in to St. Louis to spend the weekend with me. When you’re in a long-distance relationship, finding time to see your partner in person is a really big deal. Needless to say, I was so excited about the surprise visit. Plus, it meant we’d be together for Valentine’s Day.

So far, so good. But remember – we’d only been dating for about a month and a half by this point. No matter how much time you spend on the phone, you can only be so invested in someone after 45 days. It just isn’t a very long time.

Since he was coming in town, it was obvious we’d be celebrating the holiday. And I also knew we’d be exchanging gifts. What I didn’t know, however, was what Sean would be getting for me.

It started in the morning. He came over with roses and chocolate covered strawberries. Then, we went to an extremely fancy dinner. The bill was close to $100 (and remember – we were in our early 20’s.) Then, it was onto the gift swap.

I opened his first. It was wrapped beautifully, with shiny paper and ribbon. Meanwhile, I’m pretty sure mine was just covered in newspaper. But, OK, fine. He spent more time on the gift-wrap. No big deal.

Then… I open it.

It was a gorgeous (and clearly expensive) musical jewelry box. And not just any jewelry box – a custom made one. Glossy black lacquer, hand painted roses, and fabric-lined interior. When I opened it up, it played one the tune of one of my favorite love songs.

Later, I’d find out the actual cost, which was around $300.

The Awkward Part

I was shocked. Later, he would actually tell me that he thought I disliked the gift because of my reaction. I think I said something like, “Uh, Ok. Wow. Thanks.” And then I set it aside.

In his mind, it seemed like I was unhappy with the gift. Like, maybe I was disappointed. In reality, it was the exact opposite. I was just utterly shocked that he’d gotten me such an elaborate gift when we hadn’t even slept together yet.

And, in all honesty, I was thinking about my gift to him. You know, the one wrapped in newspaper. I opened his first, which meant it was now his turn.  

With my cheeks burning in embarrassment, I handed him his for what had to be the most awkward Valentine’s Day gift exchange ever. Because it was… a DVD.

Now, granted, this was pre-Netflix, so DVDs were still all the rage. But it was a $10 gift. Ten dollars! Compared to what he got me. The roses, chocolates, fancy dinner, custom-made jewelry box. He must’ve spent well over $400 altogether.

To this date, it was the most awkward Valentine’s Day I’ve ever had.

Life Lesson

Sean and I ended up dating for a very long time. What started as a high school friendship turned into a very serious romance. All said, it wasn’t a detrimental Valentine’s Day. Just a really awkward one.

Looking back now, I think I had the right idea. We hadn’t been dating very long. A $10 gift (and one that wasn’t super romantic) was appropriate. His, on the other hand, was way too over the top.

So, my best advice for all of you would be this: your gift should reflect your current relationship. Not the one you want to have.

What was your most awkward Valentine’s Day? Let me know in the comments below!

As always, my loves, thanks for reading!


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  1. avatar
    Mind Beauty Simplicity says:

    oh my gosh – this is why i find gift giving so awkward sometimes. either someone goes too overboard and the other feels bad / inadequate. these types of stories are so fun to read! maybe i should share some of my awkward dating stories for valentines day as well….

    1. avatar

      Yes, those are always fun to read!!

  2. avatar

    I was dating this guy, and we had an extremely rocky relationship. I had brought up that I wanted to break up in January, and somehow he convinced me to stay with him. He was a workaholic, so we didn’t spend that much time together. He had originally told me that he was going to be busy working on Valentine’s day, and since our relationship was rocky to begin with, I wasn’t really thinking of getting him a gift. The day of Valentine’s day, he ended up telling me that he got out of work. Not only did he get out of work, but booked a reservation at a fancy restaurant, and when I sat down, I saw he got me a gift! It was all out of left field (especially with how our relationship was going at the time). He ended up getting me a tiffany’s necklace, and I sat there awkwardly, because I didn’t get him anything! We ended up breaking up about two months ago, but when I think about it, I kinda wish I got him at least a little something (even if he was kinda terrible)

    1. avatar

      Wow, that is incredibly awkward! I thin you may have me beat.

  3. avatar

    Oh my god, that’s one thing that I hate about gift giving.. I always feel super innapropriate not knowing if i’m above or beyond range xD
    Though I don’t believe you gotta compete for having the priciest or anything, it’s okay if it’s not the same price and all that; maybe one just got more means than the other at the time.

    The gift sounds absolutely stunning! the type of gift I would’ve had kept even after the breakup- no way!

    1. avatar

      Lol – I actually do still have it. And I use it frequently. For all his faults, he gave some of the best gifts I’ve gotten, all of which I’ve kept.

  4. avatar

    Wow thank you for sharing your story. He valued your relationship and appreciated your worth. You knew what he liked and valued him too. Yes, his gift might be over the top, but I appreciated that he took the time to consider getting you more than just roses or chocolates or even a stuffed animal. These are the most cliche and easiest to give although I appreciate each. 😍 He put thought to your gift for sure. 🤗

    Pastor Natalie

    1. avatar

      That’s definitely true! It was more that I felt uncomfortable about how little mine was in comparison.

  5. avatar

    Oh, wow that’s an amazing gift! But yes, super awkward! My husband got me absolutely nothing for our first Valenetine’s. He had already stated he thought it was a commercial holiday, blah blah so I knew he wouldn’t get me anything. But I wanted to get him something anyway so I got him some nice cologne. Which I had to exchange because it was one he wasn’t crazy about. He felt really bad about getting me absolutely nothing and showed up two days with a big bouquet of roses and an apology. Honestly, I think it led us to to understand that the relationship was about more than special occasions and how we acted on them.

    1. avatar

      It’s good that he told you upfront his thoughts about Valentine’s Day. And it sounds like you weren’t expecting a gift but rather just wanted to get him something anyway.

  6. avatar

    Oh my haha! That would be an awkward gift exchange. His heart was certainly in the right place, but I think sometimes people go overboard when they want to impress a date early on and it doesn’t always hit the mark quite right. My husband and I actually started our relationship long-distance as well. He was in Florid and I was in Virginia. We met at a wedding in Georgia and dated long-distance for the first full year of our relationship before he decided to move here to be with me. It was hard, but 100% worth the challenges. In fact, we always say that we wouldn’t have the strength in our marriage that we do today if we hadn’t been in a LDR. But our first Valentine’s Day wasn’t spent together. He worked until pretty late and we logged on Skype to watch Spy Kids together before falling asleep halfway through from how late it was. Not necessarily romantic – but we’ve made up for it on other V-Days since then (however, we never do gifts on this holiday at all)!

    1. avatar

      That’s a cute way to spend a holiday together when doing long-distance!

  7. avatar
    According to Chren says:

    Oh no! This is an awkward exchange, but a very thoughtful gift. It’s surprising though that he chose such an expensive gift for the first holiday together.

    1. avatar

      I thought so too! But, he had a tendency to go overboard on gifts.

  8. avatar

    One month into dating my boyfriend, he gave me chocolate and maybe something else for Valentine’s Day. I got him nothing… I told him beforehand though that I wouldn’t and he still got sad on Valentine’s Day!

    1. avatar

      Aww! That’s a good lesson though on why it’s always important to discuss expectations ahead of time!

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30ish Lifestyle blogger, relationship "expert," and modern-day agony aunt.
Sometimes humorous, always honest.