If you share this struggle, here is some advice on approaching your Valentine with confidence and charm.

When is the best time to ask them to be my Valentine?

Timing is a very important piece in the asking part of Valentine’s Day. Asking too late can make someone feel like a last resort. However, asking too far in advance might be risky. What if they forget about it? Or what if they have second thoughts?

Although timing is key, it depends on the relationship between you and your crush. For example, if you and your Valentine are already dating, then there is no need to ask early, because it is almost guaranteed they will say yes. For a couple, asking a few days before, or on Valentine’s Day, is a great way to go. 

“If you have been talking for a while, then I would just ask them to be your girlfriend or boyfriend on Valentine’s Day as well as your Valentine,” junior Aiden Mahoney said. 

On the other hand, asking your crush or friend to be your Valentine comes with different timing. Two weeks in advance is too early, but asking on Valentine’s Day is way too late. Around a week in advance is best to give them space to think about it and prepare for your plans. 

  “Don’t do it the day of,” sophomore Hyewon Kim said. “Because what if they already had gotten asked out, or they just don’t like you?” 

How can I ask them to be my Valentine without it being awkward?

After you have guaranteed the timing and gift, it is time to put everything together for the production. There are a few simple things you need to make the proposal perfect: confidence, straightforwardness and authenticity. 

For those who are not into big displays, ask them somewhere quiet and enclosed like their house or a restaurant. No matter where the proposal is, your Valentine will love the thought and authenticity that you bring to the proposal. 

“Going to a park or somewhere alone on a date is cute and romantic because I wouldn’t want to get embarrassed anywhere,” sophomore Merisa Zdralic said.

However, for those who are not afraid of cringy proposals, it is your time to go big or go home. Instead of making a small gesture, taking your Valentine out in public on a date with a poster, gifts and flowers is a great way to surprise them, and maybe even get a round of applause. Imagine walking at school and getting tapped on the back to turn around and see your crush standing with an obnoxious poster and huge teddy bear waiting for you.

“I wouldn’t mind him doing something extravagant, but I also wouldn’t mind him doing something small,” junior Maja Elina-Rothe said. “I just want to know that he cares and puts effort into it.” 

What are we after Valentine’s Day?

After the perfect day and date, most will feel content with the conclusion of the day. However, for those who are not already a couple, it may be hard to know where to go from there. 

Communication is major at this point in your relationship. Knowing whether you are talking, dating or just friends is important in maintaining a strong relationship.

“After being each other’s Valentines, I would just talk to him to make sure we’re on the same page, and if we both like where it is going, then start dating,” Elina-Rothe said. 

Even if one person decides the way you are headed is not right, talking to each other is much more important than letting a relationship fall apart. 

If you were not feeling the “butterflies in the stomach” feeling, then calling or talking to your Valentine about just being friends is a safe way to go. Even though it may feel nerve wracking, having an honest conversation is less painful than being stuck in a relationship you do not want to be in. On the other hand, if you feel sparks go off whenever you are with them, then asking for another date is a good way to keep the relationship moving forward. 

Don’t be afraid to send in some struggles you may also have to [email protected], others may share them too and it is okay to ask for some advice!