I Got A New Boyfriend Two Days Before Valentine’s Day… Yeah, It Was Awkward


A new BF right before Valentine’s Day? A little awkward. Source: ShutterStock

Even though Valentine’s Day is this super romantic holiday, it makes 100% sense to me why you probably never want to have your first date on Valentine’s Day. Actually, make that the weeks leading up to Valentine’s Day. There’s so much pressure around the holiday that before you know it, you start panicking about what you should be doing. Believe me, it gets awkward.

During winter break from college, I talked to this guy from school all the time. I was excited to hang out in person again once we finally got back to school toward the end of January. Well, just a few days after getting back, we kissed (awwww) and basically entered a kind of temporary friends with benefits stage.

I had always kept the lead up to Valentine’s Day pretty guy-free, partially because a whole holiday about flirting and sharing feelings just seemed like a goldmine for awkwardness. But here I was in the first week of February with a cool guy, but no real clear definition of what was happening. Yeah, I didn’t like that things weren’t crystal clear.

So what did I do? Well, we decided to officially start dating! Two days before Valentine’s Day! In my mind, this was a great way to get rid of all that confusion that I had about how the two of us were supposed to celebrate the holiday. In reality, it was a super awkward decision.

I realized this about a day later (aka February 13) after the initial “YAY!” factor wore off. See, when we were just FWB  I had been worried about whether or not I had to buy a gift for him. I guess I thought that if we were a real BF/GF, I would immediately know what to buy him for Valentine’s Day. Obviously, this did not happen.

Being a college freshman, I had no means to get anywhere off campus, so since we had only been dating for officially 36 hours, I ended up with… nothing. However, despite being in the same boat as me, he somehow managed to get me candy and a card. So basically, empty-handed me felt like the worst. So much for this awesome plan to be dating on Valentine’s Day!

To kind of make it worse, his birthday was a couple days later, so it was like a two-for-one of personal holidays that I was totally unequipped to deal with. I felt pretty bad about the whole Valentine’s Day situation, so I felt even more pressure to do his birthday “right.” The thing was that we were still in a “getting to know you” newbie relationship, but I was letting the holidays make me feel like it all had to go into warp speed with grand gestures. I think I ended up getting him a shirt that he never wore, like ever.

Looking back, we probably just should have made a pact to skip Valentine’s Day. We liked each other and I think deciding to date would have happened anyway, but the Valentine’s Day pressure definitely accelerated it. While I’m glad things worked out for me, definitely don’t feel like you need to sort out your entire love life by February 14.

Seriously, you don’t want to have any regrets once you wake up on February 15 and your thoughts are perhaps a little less clouded by Cupid. Basically, don’t let the calendar dictate your relationship or you’ll be a total ball of awkward stress (just like freshman me).

Have you ever felt pressured to define your relationship because of Valentine’s Day or otherwise? Would you ever start dating someone right before a major holiday? Do you think it even matters? Tell us in the comments. 


The Traumatizing Moment That Made Me Hate Valentine’s Day

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Posted in: Confessions
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