I (24M) need advice about whether it’s okay to give my crush (21M) flowers on Valentine’s Day.

I’ve had a crush on him since sophomore year in college. The first time I saw him smile, I couldn’t help but be drawn to him. Back then, he had a boyfriend, and even though there were chances for us to get to know each other or be friends, I decided to keep my distance. I respected their relationship and didn’t want to overstep since my feelings for him were strong, and I knew I didn’t want to cause any trouble.

In junior year, after a lot of reflection (and encouragement from my friends), I decided to anonymously send him flowers and some cookies I baked. At the time, my friends assured me it wasn’t inappropriate because I wasn’t trying to take him away from his boyfriend just letting him know someone admired him. He accepted the flowers and cookies and thanked me through the mutual friend who delivered them. That gesture felt like enough for me back then.

Now we’re seniors, and he’s now single. They have split months ago, and in December, I started following him on Instagram. I’ve been interacting by reacting to his stories, and on New Year’s, I sent him a greeting. He didn’t reply, though, so I decided to just stick to reacting to his stories since there’s no natural way for us to start a conversation.

I’ve been thinking about confessing my feelings. Most of the people I’ve talked to friends and even strangers I’ve had random conversations with have encouraged me to “shoot my shot” rather than live with a “what if.” One friend even told me last year, “It’s not about whether he likes you immediately it’s about whether he gives you the chance to make him fall for you.” That advice has been stuck in my head ever since. One of my friend that is also a friend of my crush even offered to help set up a moment for me to confess.

Here’s the thing this would be the first time I’m giving flowers to someone I like romantically in person, and it’s nerve wracking. I’ve never pursued anyone before, and I don’t want to make him uncomfortable or put him in an awkward position just to get a response. I genuinely admire him and want to be honest about my feelings, but I also overthink what he might feel in that moment. There’s also some urgency because I’ll be going abroad soon for my OJT somewhere between February 16–29, though the exact date of departure isn’t set yet and I’ll be back by the end of June. I feel like if I don’t take this chance now, I’ll regret it later, but the timing adds extra pressure it will be our graduation on July so there no other chances left.

I’ve also heard people say LGBTQIA or gay relationships can work differently. I don’t fully understand the nuances yet, but from what I’ve been told, things like courtship and getting to know each other can overlap more than they do in straight relationships. In my head, if he gives me a chance, I’d approach it by getting to know him first but does “getting to know him” already count as courting? I don’t know how all of that works, but what I do know is that I want to express my feelings while being as respectful as possible.

So, should I go for it? Is giving him flowers and confessing my feelings on Valentine’s Day a good idea? I really want to do this, but I want to make sure it comes across as genuine and not pushy. Any advice would be appreciated.