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!
*Note: Names have been changed, as always.
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.
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.
Related Read: 5 Great Valentine’s Day Ideas at Home
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.
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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