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Hint toward your feelings.
Be aware that he might not pick up on your feelings if you’re not outright. You might be too shy to come right out and say, “I like you.” If this sounds like you, you might want to hint at your feelings instead of putting your feelings on the line. You can hint your feelings by saying something like, “I really like spending time with you” or, “It would be fun if we were lab partners.”
Text him.
Texting keeps your conversation private and gives you time to think. If you’re shy, it might be difficult for you to go up to the guy, especially if he’s around other people much of the time. Texting can be an easier way to flirt and interact with him without having to worry about awkward pauses or not knowing what to talk about. If you’re texting back and forth with him, use the opportunity to slip in some hints. Just talking to him over text shows interest. If you want to go a level up, say, “By the way, I think you’re cute.” You can even come right out and say, “I like you” over text once you build your courage.
Write a note.
Start by giving him a note and see if he writes back. Maybe going up to him and saying that you like him might overwhelm you or fill you with fear. If you see the guy at school (or out of school) regularly, you might want to slip him a note. This way, you won’t have to stumble over your words or ‘blank out.’ If you write a note, you’ll also be able to write a few drafts before settling on one you like and are ready to give to him. If you pass a couple notes, you might want to tell him you like him in the next note. Spend some time writing your note and deciding what to say. You might want to make it short and sweet or lay out your feelings. It’s up to you what you want to say in your note, just make sure you tell him you like him.
Catch his eye.
Making eye contact is an easy and subtle way to let him know you like him. Make the most of your opportunities to look him in the eye. For example, if he says hello to you, look him in the eyes while you say hello back. You can act a bit coy by dropping your gaze, then looking back up at him with a smile. If he makes eye contact back, chances are he finds you attractive. Try to hold your gaze with him for one to two seconds. Don't stare though! See how he responds––does he smile back, look away or just stare vacantly? Try to gauge his willingness to interact with you.
Send him something from a secret admirer.
Try to ask him about how his secret admirer makes him feel. If you want to show him you care but just cannot get yourself to come out and say it, send him something and sign it from a secret admirer. Send him a favorite food (like hot sauce or chocolate) or something you know he’ll like. Send a card and simply sign it, “Your secret admirer.” If you send him something from a secret admirer. You will likely need to tell him at some point it was you.
Invite him to spend time with you.
It’s okay for you to ask a guy to hang out too and make the first move. Maybe you’re too shy to come right out and say, “I like you.” Another option is to invite him to spend some time with you. Spending time with him will help you gauge how he feels about you and whether you should start spending more time with him. This shows him that you want to spend time with him and get to know him better. For example, ask him to go to a dance or to a sports game with you. Say, “I got two tickets to see the basketball game on Friday, and I was hoping you’d be free. What do you say?”
Set a deadline for when you want to tell him.
Decide that you want to do it, then act on it. As a shy person, you might do best by preparing to tell him you like him. For example, decide on a specific day and time to tell him you like him. Do something to help you follow through, like writing it down in your planner. For example, if there's a party on the weekend that you know he's going to be at, tell yourself, "All right. I'm going to keep an eye out for him. When I see him, I'm going to wander over and bump into him, then I'm going to tell him."
Choose a moment when he is by himself.
No need to have his friends eavesdropping or casually listening in. As a shy person, you don't need an audience! He will also appreciate your tact and respect for his privacy. Read the situation and pinpoint an appropriate time to talk. If he’s in the middle of talking to somebody, wait for a few moments. Once they walk away, it’s your chance to approach him.
Get to the point and tell him.
Don’t let your conversation drag on too long without telling him you like him. He might become disinterested or the conversation might fall flat. You can start by saying, "Hey Xavier, you got a moment? There's something I'd like to say to you." Then follow by saying, "I've been enjoying spending time around you a lot lately. And I just wanted to let you know that I like you. I was hoping you might feel the same way."
Find out if he likes you.
Your job is a lot easier if you know he likes you. If he smiles at you or goes out of his way to see you or spend time with you, these are good signs that he’s interested. He might tell you he likes you or you might find out from a friend that he likes you. Your biggest job now is building your confidence to tell him you feel the same way. If he doesn’t know who you are or sees you as a friend, then you have some more work to do.
Notice if he flirts back.
Notice how he responds and whether he moves toward you or moves away from you. As a shy person, you’ll probably want to be flirty before going up to a guy and telling him you like him. Gauge his interest and see if he flirts back. In many ways, “actions speak louder than words” so let your non-verbals do the work. Try some basics of flirting such as laughing at a joke he makes or touching him lightly on the arm. This can drop the hint that you’re interested. You don’t have to be over-the-top. Being subtle can almost be better, as you might carry some mystery.
Think about the worst-case scenario.
He might say he doesn’t feel the same, but it’s highly unlikely he’ll make fun of you. Part of your shyness might be imagining the worst that could happen. But what really is the worst thing that might occur? Be realistic and rational. If he does embarrass you, this reflects more on him being a jerk than anything else and others will see that, too.
Make telling him a challenge.
Instead of making the situation difficult or scary, frame it as a challenge. Are you up for the challenge? Whatever happens, you’ll know you pushed yourself out of your comfort zone. Give yourself credit for trying, even if it doesn’t turn out the way you want it to.
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