Should I Tell Him I Like Him? 8 Questions To Ask Yourself Before You Confess Your Feelings

Having a crush can be really hard. For many people, it’s almost embarrassing to face the fear of rejection if it doesn’t go the way you want. Still, keeping your feelings on the inside will only lead to hurt if your crush moves on to someone who was more vocal about their intentions. Plus, your feelings could be reciprocated and by not speaking up, you could be missing out on an amazing romance! Here are some things to consider if you’re on the fence about asking him out.

  1. How strong is your friendship? If you’re close to this guy, will a confession of feelings scare him away? It’s very tough, as those who were good friends before being romantic make incredible couples. It’s also great to date a friend since you won’t have to worry about impressing him. He already knows who you are and like you for you. The best way to approach it is as follows. If you’re feeling a real sense of chemistry, say something flirty joking about how he’s so amazing that it’s hard not to catch feelings on occasion. His reaction to this statement will tell you everything you need. If he blushes or asks why that’d be a bad thing, you’re in. If his reaction was negative, you’ll know where you stand.
  2. Is he standing in your way from other dating opportunities? It can be hard to be so involved with a crush that you’re blinded to the advancement of others. If this crush is holding you back or keeping you single, then it’s time to come clean. Mention how you feel and move on if he’s not that into you. Crushes should have a time limit. That way, if it wasn’t meant to be, you won’t blame yourself for wasting years on a guy that broke your heart.
  3. Is the crush safe? Having crushes on teachers can be normal, but you should never take it to the next level. Same with having a crush on your boss or someone you work with. Never put someone in a potentially awkward situation if they don’t have to be. If you’re embarrassed about the crush, that should be a red flag that something’s not appropriate.
  4. Do you see the relationship going anywhere? If he lives in Canada and you live in the United States, do you think you’d make sure to visit once travel resumes back to normal? All relationships need a gameplan. If you don’t see a potential relationship thriving, then maybe it’s better to try and end your crush. But if this is someone worth making an effort for, then that changes everything.
  5. Do your friends have a crush on him? It can be awkward when you and a friend have a crush on the same person because no matter what, that’s another set of feelings involved. If she’s confided in you that she likes him, it’s best to take things slow. Admit that you do too so that everyone’s on the same page. Then, see how deep of a crush it is. Does she just think he’s attractive? Or, does she think he may be great husband material?
  6. Are you ready for a relationship? If he likes you too, that’s the next step. Sometimes the chemistry can be all there but the situation just doesn’t work out. Maybe you’re too busy with your job right now to devote time to a relationship. If you don’t think anything will happen between you two, might as well let it be a secret.
  7. Are the two of you actually compatible? Sure, a lot of people had crushes on Jonathan Taylor Thomas when they were growing up, but nobody really knew what he was like in person. If you’re only crushing on him for his physical looks, it’s not wise to tell him. But if it’s his personality and interests that are attractive to you, then you should tell him. Having something in common with him is also a good way to tell that your feelings are sincere.
  8. Can I recover if this backfires? Sometimes we think we’re getting all the good signals, but as it turns out, we were all wrong. That’s the risk you take in telling someone you like them. Play through the scenario where he tells you he’s not feeling the same. Is it too much? Does it make things uncomfortable, if you have to see him around a lot? It seems sad to think about, but you always need to think about your feelings. If having him reject you would lead to a severe dip in confidence or an awkward situation, you might want to wait for a better time.
Karen Belz is a New Jersey native who is currently living in Maryland. She has a Bachelor’s Degree in Speech Communication with a focus in Broadcasting and Print Media Studies from Millersville University of Pennsylvania. Since graduating, she has written for sites like LittleThings, HelloGiggles, and Scary Mommy and is currently an e-commerce editor at Bustle.

When she's not writing, she enjoys making her phone run out of memory after taking too many photos of her dog. You can find her on Twitter @karenebelz or on Instagram @karenbelz.