How should I tell my friend that I love him?

[Silly Metal Latina]

I (25F) have this guy friend Henry (27M), I call him Hank, and I’m in love with him. It’s not a crush or something like that. I love him and not just as a friend, although he is a wonderful friend! He makes me laugh, he always seems to know just what to say of nice gesture to make to cheer me up. He’s a big cheerleader of mine, and I feel like I can confide anything to him. He’s really one of my best friends and I have messed this up by falling for him.

I have known him since high school although he and I weren’t close back then. In fact, I really couldn’t stand him and he definitely was not my type. Don’t get me wrong, he’s an attractive guy but back on high school he was an immature jerk, class clown type who cared more about getting high and playing in a band than getting good grades. The reason I knew him at all is because his sister Angie and I have been best friends since we started high school.

Well he was in the Navy after he graduated high school and I didn’t get to see him much until around a year and a half ago when Angie had a party. Boy had he grown up a lot since school! He was still irreverent and funny but now he was much more mature. He even apologized to me for some of the dumb things he did back when we were kids. 

Of course I wasn’t immediately into him at that time although I still thought he was attractive. Even more so now but I digress. He was very nice and I would see him from time to time when he’d meet his sister for drinks or hang out with us.

When Angie moved out of town about a year ago, Hank and I started to get a bit closer. I think at first we bonded over our mutual sadness over Angie moving so far away. So he and I started to become friends and he’s really is such a kind and thoughtful guy. We have become concert buddies, we hang out at least every other weekend. I feel like we just vibe so well!

He has done so many kind things for me that it’s unbelievable. I think that’s why I started to fall for him. It really got serious back in March when I had an interview for the job I have now. He sent me a really thoughtful text telling me he knew I’d kill it in the interview and that they’d be lucky to have me.

After that I knew I was getting feelings for him. I am in this position totally unexpectedly. This wasn’t my plan at all but here I am. I do really love him. I think we could be so good together. But we’re are already good together as friends and I’m afraid to mess that up! I’m also terrified of him saying no and how crushing that would be! Of course I’ve read a ton of stories of people being in this position but I never thought I’d find myself in it!

So if you were in my position would you tell him your feelings? One of my other friends says she sees the way he looks at me and it’s definitely clear to her he’s into me. My mom says that if he was interested he would have stepped up by now. But I know his dating history and like mine it’s not great so maybe he’s scared of getting hurt too?

What would you do? I’ve had some ideas how I could tell him but last time we went out I was tongue tied when I thought I was going to bring it up.

 

 

[Wiseman2]

He may already have a crush, who knows? Since you're pretty close try to run it by him in a light sort of way such as "have you ever thought about us dating?" See how he reacts. Keep it light so you can back down and not make it awkward.

[Batya33]

Is he single ? I wouldn’t tell him. Ask him out on a proper date. He’ll get the hint 

[boltnrun]

Confessions of feelings are cute in the movies but in real life? It doesn't always turn out how you imagined.

Instead, how about offering to cook him a great dinner? If he agrees, dress in a flattering way (NOT sexy!). Compliment him and talk about his interests. Then say something like "I think it would be great if we went out on a date. What do you think?"

[Coily]

Poor guy may think he's in the friendzone.

Seriously, you should ask him on a date, now it doesn't have to be a candle lit cliche; but it should be blatantly obvious it's intended to be a date. The last few decades have messed up the "a guy would just step up", so it would behoove you to make the effort. What's the alternative? Never knowing if there could be something there, and then getting invited to his wedding and have to sit there wearing a mask.

[smackie9]

Dress pretty, be flirty and suggest you two go out on the town. Let things happen organically. 

[Kwothe28]

2 hours ago, Silly Metal Latina said:

So if you were in my position would you tell him your feelings?

Have you tried flirting first? "Confessions" rarely work in a reality. They are too abrupt and can take the other person by surprise. For example, he maybe thinks you are only friends. Just "dropping the bomb" on him would shock him. Maybe flirt a bit first and feel the situation. Say a few flattering words and see how he takes it. And if he takes a hint and flirts back.

[Silly Metal Latina]

2 hours ago, smackie9 said:

Dress pretty, be flirty and suggest you two go out on the town. Let things happen organically. 

Ha ha. I’m not much of a “pretty” dresser but I was thinking of asking him if he’d like to go to dinner. We have never really had a situation where we went out and ate just the two of us. We’ve been out to dinner in a large group of friends a few times. The times we’ve gone out alone have all been public places like concerts, amusement parks that sort of thing. We have hung out at my apartment or his house alone a few times too but that was really chill and neither of us seemed like we were trying to make it into something more at the time. I think if I asked him out to have a quiet dinner alone he would understand that it’s a date. Or maybe I’ll just ask “Hey would you like to go on an actual date with me?”

[Silly Metal Latina]

3 hours ago, boltnrun said:

Confessions of feelings are cute in the movies but in real life? It doesn't always turn out how you imagined.

Instead, how about offering to cook him a great dinner? If he agrees, dress in a flattering way (NOT sexy!). Compliment him and talk about his interests. Then say something like "I think it would be great if we went out on a date. What do you think?"

I like this idea! I agree that real life isn’t like the movies too! 

[Silly Metal Latina]

3 hours ago, Batya33 said:

Is he single ? I wouldn’t tell him. Ask him out on a proper date. He’ll get the hint 

Oh yes he is single! I would not think of saying something like this to a guy who was involved with some other girl. I’ve been cheated on in the past and it’s the most awful thing you can do to someone.

[boltnrun]

4 minutes ago, Silly Metal Latina said:

I like this idea! I agree that real life isn’t like the movies too! 

Cool! I hope it all turns out great. 

[Wonderstruck]

Your profile picture and username are so cute and endearing. ❤️

And you seem so lovely. I'm rooting for you, sis!

I hope that you come back and update everyone on how it went.

[Wiseman2]

1 hour ago, Silly Metal Latina said:

. Or maybe I’ll just ask “Hey would you like to go on an actual date with me?”

That's fine. It's light and fluffy enough to get the point across without awkward flirting, dressing up or inviting him to your place for romance which is all too vague and confusing.

You've been friends a long time and should be able to just make a suggestion.  This way it's not awkward, not "confessing" anything and simply laying your cards on the table.

[Silly Metal Latina]

3 hours ago, Wonderstruck said:

Your profile picture and username are so cute and endearing. ❤️

And you seem so lovely. I'm rooting for you, sis!

I hope that you come back and update everyone on how it went.

Awww thank you! I’ll have to see because he and I talked yesterday and he’s got a lot on his plate right now. He’s helping out with his mom who was in an accident earlier this summer and isn’t in good health, he works a lot and he’s rehabbing the house he bought last year pretty much by himself. I feel I need to figure out a good time to talk to him but I think I’m going to start by making him some dinner this Friday for when he comes home from work.

[shouldhavelearned]

Not sure this is love 

[catfeeder]

I'd craft myself a Plan B for how I'd handle it If friend doesn't respond as I would hope. This would allow me to regroup and preserve the friendship if possible.

For instance, what if I learn that he has an interest in someone else or is gay, or just plain isn't interested in ME?

If I can consider the worst of the worst yet I still feel that a possible romance with this guy outweighs all possible risks, then I'd feel proud for preparing myself. This might actually help me to feel more brave.

Head high, and best of luck!

 

[Silly Metal Latina]

1 hour ago, shouldhavelearned said:

Not sure this is love 

May I ask why? I mean I can tell you for sure that I love him.

[boltnrun]

2 hours ago, Silly Metal Latina said:

May I ask why? I mean I can tell you for sure that I love him.

I was wondering the same thing. What are you basing your opinion on, @shouldhavelearned?

[shouldhavelearned]

Mainly because it doesn't sound like you've dated or talked with him about any of this. You don't know how he works mentally or what he thinks toward you.

[NighttimeNightmare]

13 hours ago, Coily said:

Poor guy may think he's in the friendzone.

Seriously, you should ask him on a date, now it doesn't have to be a candle lit cliche; but it should be blatantly obvious it's intended to be a date. The last few decades have messed up the "a guy would just step up", so it would behoove you to make the effort. What's the alternative? Never knowing if there could be something there, and then getting invited to his wedding and have to sit there wearing a mask.

I agree with this. I can say, as a guy in my 30s, now adays it seems way too risky to make a move on your friend, or a woman in general. So I don’t agree with your mom that he “would have stepped up by now.” 
 

I was just in this same situation where I developed feelings for a friend, I never ended up asking her out for multiple reasons but a major one was I didn’t want to be “that guy” who couldn’t “just be friends” with a woman. (Even though I have several close platonic female friends). 
 

I don’t know what this new energy is regarding all of that but it’s almost like if you’re a guy and you misinterpret something you’re seen as a predator. So it’s just easier for decent dudes to err on the side of caution and never say anything. 
 

I had a convo with some guys recently about this and they all said they appreciate when the woman steps up because of this 

[Lastchallenge]

Don’t over think it. I would say just go out like you always do  and maybe start with something small like holding his hand. 
if he likes it you’ll know 

[Lastchallenge]

5 hours ago, Silly Metal Latina said:

May I ask why? I mean I can tell you for sure that I love him.

Don’t mention love for now just okay it smooth 

[boltnrun]

7 hours ago, shouldhavelearned said:

Mainly because it doesn't sound like you've dated or talked with him about any of this. You don't know how he works mentally or what he thinks toward you.

That has nothing to do with HER feelings toward HIM. That's just saying it isn't clear if HE loves HER romantically.

[Silly Metal Latina]

9 hours ago, boltnrun said:

That has nothing to do with HER feelings toward HIM. That's just saying it isn't clear if HE loves HER romantically.

Thank you! I know how I feel about him! I just don’t know how he feels about me!

[shouldhavelearned]

Yeah, loving him without really knowing him.

 

That makes no sense to me.