Should I Tell Him How I Feel? Here’s When To Confess Your Feelings

“So Adam, there’s this guy, and I’ve known him a while, and I like him a lot, and I think he might like me too. But I’m not sure because he hasn’t said anything, and he’s really difficult to read (like every guy ever). We’ve got plenty in common, and every time I see him, I get butterflies in my belly, and our connection grows stronger. I don’t want to make the first move; I want him to pursue me, but I’ve been waiting already, and how long am I meant to wait for him to see the obvious and get his act together? Should I keep waiting, or should I tell him how I feel so I can stop living in this constant limbo of ‘he likes me, he likes me not’ and move on with my life?”

Is this your story?

In your school days, it would be normal to have endless conversations with your girlfriends about the boys you liked (and didn’t like) and ask, “should I tell him how I feel?” You probably wouldn’t end up spilling your heart out to the boy in question, but your friends would talk to his friends, and if he liked you back, he’d ask you out.

But then we all grew up, and the mere thought of telling a guy or his friends how you feel is mortifying. Heck, you might not even feel comfortable telling your girlfriends about it. It’s not like middle school, where if a boy doesn’t reciprocate your feelings, you’ll probably be over it and crushing on someone else by the next period. Our feelings usually grow deeper as we get older because they come from a more considered and authentic place. And with that comes greater risk.

Is it okay to tell a guy how you feel? How do you let him know how you feel? What even happens when you tell a man how you feel about him?

What if he doesn’t like me back? Or, what if he does like me back? Then what?

In this article, I’m breaking down the signs you should and shouldn’t tell him how you feel. Ready for answers?

Should I tell him how I feel? 7 signs you shouldn’t

1. You don’t know each other that well

When you’re 12 years old, it doesn’t matter if you’ve known each other for five minutes or five months – it’s perfectly okay to tell a boy you like him. Why? Because it’s the nature of young kids to move fast with their feelings. One day you like Brad. The next week you’re totally over Brad and into Codey. But then Codey moves away, and Jack captures your heart. It’s a miracle if your parents ever managed to keep up with the 411 of your crushes.

But as you get older, this speed in developing and sharing your feelings becomes less and less acceptable. If you met a guy on the first day of a new job, then confessed that you’re totally into him by lunchtime, he’s probably going to be a little (okay, a lot) freaked out. And you would be too!

So, if you don’t know the guy in question that well yet, I’d recommend holding off on telling him how you feel. You want to have known him for at least three months to avoid scaring him off too soon.

2. Your friends don’t like him

It’s easy for us to be blindsided when we have strong feelings for someone. Women, in particular, will often see and hear what they want to see and hear rather than what’s in front of them. If you know you tend to do this (look at your history with men), it’s really important to get external opinions from people you trust. What do your nearest and dearest think of this guy? Do they approve of your crush and want you to get together? Or are they warning you off him and trying to set you up with anyone but him? Are they seeing red flags that you don’t want to see?

If your friends don’t like him, then this is a sign you should not tell him how you feel, and you should start meeting other men (Little Love Step #3). It won’t be long before you’re having so much fun dating high-quality men, and it dawns on you that you can do much better than this guy.

3. You don’t feel comfortable enough to be yourself around him

How do you feel when you’re with this guy?

Do you feel like you can be yourself without fear of judgment? Do you have an authentic relationship? Or are you pretending to be someone you’re not, like, “OMG, I love fishing too,” (said no woman ever)?

If you don’t feel comfortable enough to be who you truly are with this guy, you’re not ready to have an honest conversation about your feelings. Wait until you build a stronger foundation with him, and if you never feel comfortable, then you’ve got to ask yourself why you would even want to date someone who puts you on edge.

4. He isn’t consistent

Next time you’re wondering, “should I tell him how I feel?” pay attention to how consistent he is – with you and other people.

Does he text or call when he says he will? Does he come through when he says, “drinks are on me,” at the office? If he has a dream to switch careers, is he taking steps toward those goals, or is he just talking about it? Does he show up when he makes plans, or does he bail at the last minute?

Should you confess your feelings to a guy?

If he’s not consistent, don’t waste your precious time because he’s bound to be inconsistent in a relationship with you.

5. He has told you he doesn’t want a relationship

It’s absurd how many women will have a guy tell them that they’re not ready for a relationship or anything serious and take that as code for, “the right woman can twist my arm and make me settle down.”

There is some truth in this because most men are looking for a long-term, committed relationship rather than a hookup. But there will be times in a man’s life when he isn’t in the right head or heart space for that. Maybe he has just come out of a serious relationship, or he has a lot going on at work, or some other family issues are taking a lot of his energy.

If a man tells you he doesn’t want a relationship, believe him! And reserve your feelings for someone looking for the same things you are.

6. He is always friend-zoning you

Should I tell the guy I like how I feel?

Well, if he’s doing things like calling you “friend,” “buddy,” or “mate,” and only ever hangs out with you in groups, this is a strong sign that he doesn’t have romantic feelings for you and thinks of you as firmly in the friend zone. If you’re in the friend zone, don’t tell him how you feel because your feelings are unlikely to be reciprocated.

7. One or both of you are already in a relationship

Is it bad to tell a guy how you feel? Yes, if either of you is already in a relationship with other people. It’s not only morally wrong but also incredibly unfair on the SOs in question for you to declare romantic feelings for someone who is already taken.

And you might say, “but Adam, I can’t help how I feel!” To which I would say yes, you can. Do the responsible, mature, right thing, and don’t be a homewrecker. There are plenty of amazing men you can date who are single – yes, even at your age! Granted, the dating pool naturally gets smaller as we get older, but honestly, that’s mostly because we have a clearer idea of what we want (and don’t want) than we did in our 20s. Think about it. There are probably men you dated in your 20s that you would not even entertain the idea of dating now.

Should I tell him how I feel? 10 signs you should

1. You can be yourself around him

Is it worth telling someone how you feel?

Yes, if you have feelings for a guy and you can be your authentic self when you’re with him. The only thing you’re hiding is your massive crush (and that’s okay). It’s rare to find people you can be completely comfortable with and not have to put on a mask, pretend you like or dislike certain things, or dress a certain way out of fear of being judged, humiliated, or ostracized. For example, you tell him you’re going to a Jonas Brothers reunion show with your daughter, and you’re just as excited as she is, and he playfully says, “we can’t be friends,” but he also makes it clear he’s just teasing you.

If you can be yourself around him, this is a strong sign that you already have a strong foundation for a relationship.

2. You sense he might feel the same way

Your intuition as a woman is one of your superpowers. The problem is that we’re often discouraged from trusting it, but I want you to start learning to trust it. If you have even the smallest inklings that the guy in question might feel the same way about you, then you’ve got to tell him. Don’t waste time wondering, hoping, or driving yourself to insanity! Life is short and fleeting – we only get so many days. So don’t let another slip by where you’re holding yourself back from what you want.

3. He has shown clear signs that he has romantic feelings for you

Although he might not come right out and say that he has feelings for you when a guy is interested, he will behave in a way that subtly communicates his interest. He will compliment you, go out of his way to make you laugh, keep in contact with you regularly, make eye contact and smile at you a lot, tease you, flirt with you, and touch you (in a non-creepy, appropriate way).

So if you’re getting many of these signs from him, there’s a good chance he likes you back, and you should tell him how you feel.

4. He’s a part of your everyday life already

Should I tell him how I feel?

If this man is already in your life in a big way, i.e., he’s a friend, a co-worker, or a neighbor you regularly bump into in the park while walking your chocolate Labrador, there is more urgency to share your feelings. Why? Because you see him practically every day! Your words and actions will eventually give you away anyway. In fact, he might already suspect that you like him. And if you do see him regularly, especially one-on-one, this is a sign that he might reciprocate your feelings.

5. You’re both single

As I mentioned before, the last thing you want to do is tell a guy how you feel when one or both of you are already in a relationship because that’s selfish and will only complicate things further. Who needs that kind of mess in their life? Life is messy enough!

If you’re both single and know you’re not going to hurt anyone by sharing your feelings, then this is the perfect time to do so. You’ve got nothing to lose and everything to gain. Regardless of the outcome, you’ll have a clear conscience which means no bad dating juju in the future!

6. Your futures are in sync

A lot of your (single) friends will give you bad dating advice. Like, “who cares if he’s not Mr. Right, he could be Mr. Right Now,” which is great if you’re looking for a casual hookup. But if you’re looking for a committed relationship, this is terrible advice!

If you are looking for something long-term, you’ve got to think about whether there’s actual potential for a happy, healthy relationship. Do you live similar lifestyles, share values, and have compatible futures? Knowing you’re on the same page before jumping in is important. If your futures are in sync, you’ve got one more reason to tell him how you feel.

7. You regularly hang out (just the two of you)

Do you have regular meetups and friend dates with this guy, just the two of you? If he’s already keen to spend time with you one-on-one, this is a great sign that he might see you as more than just a friend. No man will regularly make one-on-one plans to see you unless you’re really good friends. So if you’re already going on “dates,” tell him how you feel.

8. You’ve been dating other people and no one compares to him

If you’re single and looking to meet someone, you should be dating lots of guys and exploring your options. Eventually, someone will begin to stand out from the crowd, and this guy is worth exclusivity (this is what I call Little Love Step #5).

So, if you are dating other people but time and again your mind circles back to this guy and no one quite measures up to him, then this is a sign you should tell him how you feel. You’ve given other guys a chance and know what you want, so go for it!

9. You know he’ll take you seriously

The last thing you want to do is bare your heart and soul to a guy only to have him laugh, pretend he didn’t hear you or ask if he’s being Punk’D. To prevent this from happening, only tell him how you feel if you know he will react with a certain level of seriousness and compassion.

So if you have any reservations about his reaction, hold off until you know him better and are sure he will take you seriously.

10. You feel like you can’t keep it to yourself any longer!

Should you tell a guy how you feel? The final sign you should is if this secret is eating you up inside and you feel like you’re ready to burst. If this is all you can think about when you wake up first thing in the morning, when you’re on a date with someone else, and when you see him, then put yourself out of this torture and tell him! It is not worth feeling overwhelmed, anxious and sad or letting the rest of your life be negatively affected. He’s just one guy. Don’t let this crush keep you from living and leading your best life!

If you’re afraid to tell him how you feel, here’s what I want you to know:

There’s a good chance he won’t figure it out on his own

Before I started coaching women, I used to coach men, and to be honest, a lot of them will easily miss what’s right in front of them! There’s a high chance that he won’t catch on to how you feel unless you come right out and say it. Remember, he’s not going to risk rejection unless he has some clue that you’re into him.

Don’t count on him making a move (even if he likes you)

Even if a guy likes you back, he might move at the pace of a tortoise when it comes to asking you out. He’ll put it off as long as he can, which might feel like forever. Nobody’s got time for that, especially not a high-value woman like you.

If you decide to make the first move and ask him out, remember to let go of the desire to control everything and let him take charge on the first date or two. This is all part of Little Love Step #1.

You don’t want to miss your chance

Think about what could happen the longer you put off telling this guy how you feel. He could get a job somewhere else and move away. He could meet another woman. Worse still, he could develop a critical illness or even tragically die. Yes, it’s unlikely, but you never know when someone’s time is up. So don’t risk missing your chance to tell him your true feelings.

He might not feel the same way

I hate to be the one to burst your rose-tinted bubble, but if I didn’t give you honest advice, I’d be doing you a disservice. The truth is, there is a real possibility that he might not feel the same way about you, and that’s okay. Don’t assume that your feelings will be reciprocated or that you’ll live happily ever after and ride off into the sunset together on a pink unicorn.

Nothing can happen if he doesn’t know how you feel!

There is zero possibility of anything happening between you if neither of you shares how you feel. So while there is a risk that things won’t go the way you hope, the alternative is to suffer in silence and wonder “what if” for the rest of your life, all in the name of avoiding rejection. I want you to know that you’re tougher than any rejection you will ever experience.

You’ll feel better

You should tell him how you feel, even if it’s scary, because keeping things bottled up inside is not healthy! Men do this all the time when it comes to their emotions, and look how well that turns out (not well at all). We all feel so much better when we offload a huge secret. Remember Joey in Friends when he could finally share the secret of Monica & Chandler dating? Oh, the relief.

You can finally move forward

No matter how he reacts and how things progress after you tell him how you feel, you will finally be able to move on with your life. If he isn’t interested, who cares? At least you can now get him out of your mind and move on. Say it with me, ladies: “NEXT!”

Conclusion

Is there a guy in your life you have secret feelings for, and you’re wondering, “should I tell him how I feel?” Now that you’ve read this article, I’d love to know: how will you move forward?

Are the signs above saying you should tell him or hold off for a while?

Let me know in the comments below!