Asking out your crush for a Valentine’s Day date or even just a plain old date that happens to fall on Valentine’s Day isn’t something to be feared. I get that even asking your crush out is a momentous occasion and that Valentine’s Day may have a reputation for making people go slightly romance-obsessed, but it shouldn’t hold you back from asking out that guy or gal you’ve had your eye on. You just want to spend the day with someone you care about, and I can’t fault you for that, so in the name of romance and red and pink heart tchotchkes, know that asking your crush out on Valentine’s Day is a-okay and totally doable. Here are some tips to help you out:
Stop Putting Pressure on the Day
So, so what if Saturday or the day you want to take your crush out is also Valentine’s Day? So what if you wanted to go out on the most over-blown romantic day of the year? It is your right to take your crush out, no matter the day or celebration. Sure, restaurants might force the pre-fix menu on you two at an exorbitant price and there may be more run-ins with more couples, but seriously, Valentine’s Day isn’t just about that. It’s also about marked down chocolate from CVS and those cheesy boxed Valentine cards with this year’s children’s movie on it. We all know it’s blown up, but it’s not meant to put pressure on you to be over the top and romantic. It’s meant for you think about that special someone, and that’s okay if you want that special someone to be with you on Valentine’s Day.
It Doesn’t Matter Who Asks Who
I always found it interesting that many of my girlfriends felt that the guy should initiate a date. No. If it’s your crush and you feel like he or she might be special enough to share a plate of spaghetti and meatballs over candlelight like Lady and Tramp from the most romantic Disney scene ever, then you should do it. You’re not allowed to say that you missed the opportunity if you don’t take it, and you’d rather try then not try at all It’s extremely old fashioned to let a guy determine when the two of you should go on a date, because women can make that choice too. It doesn’t mean that chivalry or tradition is dead, it just means that women can hold open the door or have an opinion on where to wine and dine too.
Say It Creatively
Using the poo emoji in a text to ask your crush out does not count. I want that established. Yet, while we can’t all be Heath Ledger in 10 Things I Hate About You and bribe an A.V. nerd and the high school marching band to ask out a girl during soccer practice, we can at least put some effort to think outside the iPhone texting box. I suggest food, maybe a pizza. Who doesn’t love surprise pizzas delivered to their place of work or home? Better yet, find somewhere that makes heart-shaped pies. Is that too cheesy? Puns aside, the more creative you decide to go, the sweeter the gesture. It doesn’t have to be big per se, but it does have to be different and maybe heartfelt. Try playing off an inside joke or even just catering to something your crush likes, like pizza.
Pretend that It’s Not Valentine’s Day
Sure, February 14 might be considered the most pressure-filled romantic holiday according to greeting card companies, but did you know that it was also the day that Alexander Graham Bell applied to patent the telephone? It’s also Oregon’s anniversary as the 33rd state of the great U.S. of A. There are tons to celebrate on February 14, and while love might be on everyone’s minds, you and your crush can accept that it really is just a date and have fun without thinking too much about it. Heck, make a big deal out of the telephone while you’re at it. It’s an incredible invention that has been instrumental to modern day dating, evolving from answering machines to texting to suggestive emojis.
Use a Pick-Up Line
No they are not sleezy or too cheesy. Delivered properly, they can have the right amount of both: enough sleeze to get the message of attraction across and enough cheese to be endearing. I would stay away from any pick-up lines with punchlines about getting your crush out of their pants later, because those tend to go up in sleeze factor. Yet a nice sweet, well meaning pick-up line can at least break the ice about the follow up “will you go on a date with me?” question. Pick-up lines are so formulaic that your crush probably already knows where the conversation is headed anyway, and the ever-suave pick-up line serves to butter them up.
Have Something Casual in Mind
If you’re asking your crush out, you better have a plan for when they agree. I say “agree” because I’m optimistic of your chances, but once you have the question and the acceptance on the table, you better have some semblance of a plan to present. Think of it as a romantic business transaction. Your crush is sitting there, wanting to know what you have in mind, and now you are on the spot with only dinner and possibly a movie to suggest. That’s fine, but remember, you decided to ask your crush out on Valentine’s Day. Most dinner places will already be booked with reservations or have a pre-fix menu that will limit your palate choices, so you might have to get a little outside the box here than the usual date fare. Yes, this could be skeeball and soup dumplings, but your odds at getting a spot there might be better than trying that fancy Italian place down the street.
Get Them a Valentine Anyway
It might be your prospective first date with each other, so flowers and a big heart-shaped box of chocolate might be overkill, but I would say that even a small nod to the holiday would be sweet. That’s a “yes” to a funny Valentine card but a big fat “no” to stuffed bears from CVS. Those scream last minute. Even a box of those chalky sweethearts with “Be My Valentine?” imprinted on it would be okay. Who could say no to a date and to something simple, sweet, edible, and that comes with requests?
Just Do It
What do you have to lose? Okay, I understand that you don’t want to blow it, but over-thinking and inaction really isn’t getting you anywhere. All of the worry about the day, the place, and how can easily psyche you out, so I say, go do it. You want someone to share a low-key Valentine’s Day with, and the odds are that your crush wouldn’t mind spending Valentine’s Day with someone other than Netflix — surely, your crush would rather spend time with you obviously. I say to just go for it. Valentine’s Day isn’t supposed to be a day you’re too scared to ask out your crush. There shouldn’t be pressure. It’s all about you wanting to be with that special someone, and you can only do it, once you put yourself out there. It’s totally fine too, if your date results in cuddling in front of Netflix. That’s still in the spirit of Valentine’s Day too.
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