Ananya Sriram

The Winged Post sent out a Schoology survey to upper school students asking them to explain situations in their love lives or friendships so that the Winged  Post strategic team could offer advice. We chose five out of 62 responses to answer in this column.

The Winged Post sent out a Schoology survey to upper school students asking them to explain situations in their love lives or friendships so that the Winged Post strategic team could offer advice. We chose eight out of 62 responses to answer in this column.

Q: I’m in a situationship with a guy from a different school. I see him often, but there are always other people around. We sometimes text on Discord, but I don’t know how to get closer to him or how to “rizzfully slide in” his DMs without being weird because he sometimes ghosts me. 

It’s a great sign that you see him often, even if it’s within group settings. If your interactions often involve mutual friends, consider subtly asking them to give you and the guy you like some one-on-one time so you can get to know him individually. 

After one of these hangouts, keep the momentum going by sending him a message on Discord. Share an inside joke from your conversation or discuss a common interest you discovered. If he seems engaged, suggest a call or FaceTime session to take things a step further. Maybe even propose hanging out alone during your conversation. 

However, if he consistently ignores your messages and seems disengaged, it might be time to reassess the dynamics of your “situationship.” Remember, a “situationship” should add a little spice to your life, not extra stress. Trust your instincts and prioritize your own well-being above all else.

Q: There’s a guy I shouldn’t like because he’s not the most well-liked, but I have a mini crush because he seems thoughtful, smart, and fun to talk to. Even though there’s literally zero chance, I keep thinking about him after I see him.

First things first, consider why others don’t like him; Are there some red flags that you can’t spot from behind rose-tinted glasses? Now, ask yourself: is your crush genuine or is it a cure to your boredom? If it’s the latter, find a new hobby — try watching some rom-coms and wait until you find someone you really like. 

Say you really do like him; then why do you say that there’s a “zero chance?” Do you sincerely believe that, or are you playing hard-to-get with yourself? If you’re truly convinced the chances of you two ending up together are slim, distract yourself when he’s occupying your mind — delve into new hobbies or passions. 

But if there is the slightest chance that you have hope, shoot your shot! It’s easy to fear others’ judgment but remember that your story is yours. Get to know him, and maybe you’ll discover that he’s not what others made him out to be.

Q: There’s this kind of cute but quiet guy who I have two classes with. How should I start a conversation with him?

Eyeing a cute guy across the room or catching yourself smiling at everything he says — trust me, we’ve all been there. If you share mutual friends, asking for his number through them could be a subtle way to initiate contact. Sending a casual text about missed class notes or confusing lectures can also kickstart a conversation without feeling too forward. As you chat about class-related topics, gradually steer the discussion towards getting to know each other. Also, if you two sit near each other in class, take advantage of the proximity to strike up natural conversations.

Also, don’t underestimate the power of a genuine smile or a friendly hello when you see him in class or around campus. Sometimes, the simplest gestures can open the door to meaningful interactions. Remember to be patient and let the connection develop organically over time — you have a whole semester ahead of you! And, most importantly, be yourself. Authenticity is key to building a genuine relationship. 

Q: How do I meet someone for a-low-commitment second-semester senior before college relationship?

Maybe you saw one of your friends slow-dancing to “Lover” at Winter Ball or noticed that with college applications off your hands, life feels like a blank canvas. It’s only natural to want a relationship to solve the boredom; but pause before you jump into it. 

It’s crucial to be aware that even if you intend for it to be casual, second-semester senior relationships may get complicated — you both may end up more emotionally attached than expected. If you’re adamant, however, on meeting someone, consider people in shared activities, people you haven’t really interacted with, someone you may have liked in the past, or maybe even ask a friend to set you up. If there’s someone you have your eye on, just shoot your shot! It’s senior year, so why not?

As a warning, stay honest and transparent; make sure you both are on the same page in terms of low commitment and what you want out of the relationship. 

Whether you’re in a relationship or not, make some memories worth remembering in the second semester. 

Q: What are good ideas for Valentine’s day for someone you’ve been dating for about 11 months?

Consider a mix of thoughtful date ideas and heartful gifts to make the day memorable. For a romantic outing, try a picnic at the Municipal Rose Garden or a fancy dinner date at a favorite restaurant. Alternatively, you could opt for a cute brunch or dessert date at a local aesthetic cafe like Hanabusa Café or embrace the winter vibes with a fun ice skating date at Ice Center Cupertino.

If you both enjoy the outdoors, a hike in Rancho San Antonio, a sunset drive down Skyline Boulevard, or admiring the views from Communications Hill after getting boba could be wonderful options.

As for gifts, classic choices like flowers and chocolates never disappoint, but consider adding a personal touch with a DIY basket filled with their favorite snacks and other items they adore. A heartfelt love letter expressing your feelings and appreciation could also be incredibly meaningful, especially if words of affirmation resonate with them. Wishing you two the happiest Valentine’s Day!

Q: How do I end a relationship before going to college?

Navigating a breakup before college is tough, and it’s especially difficult to let go of someone you have so many memories with; but handle the situation with care.

I know breaking up may seem inevitable, but don’t bring it up too often. You both still like each other, so enjoy the spring and summer ahead of you and make some memories. That being said, don’t wait until the last minute to have the conversation. Both of you need the time and space to heal, even if you both part on good terms. 

Remember that communication is key, so be honest with your feelings without pinpointing the end of the relationship on each other. If one of you is more ready to move on than the other, give each other the chance to ask questions, answer the “what ifs,” and gain a sense of closure.

Most importantly, don’t remain close friends right after the breakup, even if it seems right at the time. Try to go “no-contact,” and give yourselves space. 

This may feel like the end of one chapter, but it is also the start of a new one. Take care of yourself!

Q: There is this guy who used to flirt with me a lot. I think he likes me, but I’ve been kind of mean to him lately. I think he is hurt and has stopped talking to me. Now that we stopped talking, I realized that I actually like him. He’s the only boy I’ve ever liked. He’s one of my only options. I’m grateful for anything, and I’ll take what I can get. How do I get him back?

Let’s cut to the chase. You have some serious attitude adjustments to make if you want to salvage this. Why were you mean to him in the first place? After all, you’re more likely to treat someone you like with respect, even if it is subconscious. Frankly, being rude to someone you like resembles the behavior of an elementary schooler. 

Now let’s talk about how you believe he is one of your “only options” and that you will “take what you can get.” You’re not shopping for a sale, you’re dealing with hearts. If that’s your attitude, maybe consider that what you really like isn’t him, but the idea of a relationship. Reevaluate your priorities.

If you’re set on “getting him back,” have a brutally honest conversation with him. Apologize sincerely, own up to your mistakes, and if he’s willing to forgive you, great! If not, take it as a lesson and move on. It’s better to learn now than to repeat the same mistakes in the future. 

Q: How do I talk to girls?

Let’s talk girl talk. You may feel like it’s a simple question with a complicated answer, but in reality, just trust your instincts when talking to girls, or really, anyone. 

As cliché as it sounds, be yourself. Own your charm and be playful and funny. There’s nothing more attractive than a little humor. Find common interests through small talk — a class you’re both in, something happening around you, and if you can find something interesting to say, maybe even the weather. Make sure to listen as well. Tune in to what she is saying and remember small details about her, from her favorite coffee order to a movie she wants to watch (these details will come in handy).

Most importantly, treat her with respect. Don’t talk over her and avoid saying things that could offend her. Instead, appreciate her. Laugh at her jokes, compliment her outfit or tell her she has pretty eyes. Anything that works, works!