Ask a Dude: Should I Ask If He Likes Me Back?

Hey Dude-

So basically I’ve never been in a relationship or gone on a date with a guy. Over the years, I’ve liked a lot of my friends but I’ve always been too afraid to make the first move because I feel like they don’t like me in that way. A lot of the time, though, other people can tell that I like the guy but I never bring it up to him directly, and I just always think to myself “well if he liked you, he’d ask you out, it has to be obvious that I like him.”

I’ve talked to a few of the guys later on when we hadn’t talked to each other in a while, and in each of the cases the guy admitted to liking me at the same time I had liked them. I’m just so confused now because I really like this new guy, but I honestly can’t tell if he feels the same way. I just don’t know how to bring it up to him without seeming obsessive or making things super awkward between us, but at the same time I feel like I’ll regret it down the line if I find out later that he had feelings for me the entire time.

I’m just getting such mixed messages because he always tells me how much he likes talking to me and he compliments me a lot…but at the same time I can’t tell if that’s just pure friendship or if he might feel something more too. And I just really love him so much as a person that I don’t want to ruin our friendship over this…but it’s bothering me not knowing for sure if he likes me or not!

How do I know for sure if he really is just not that into me?

-Completely Confused

Dear Completely Confused,

There’s nothing that halts the course of happiness more completely than fear we can’t set aside. Unfortunately, it sounds like your fear of rejection, and thus of getting hurt, is what’s keeping you in the “not knowing” circle of Hell. Well, there’s only so many ways to skin this cat. They all involve you being active.

We all have patterns. We all have defense mechanisms. We all have habitual behaviors that we think are the best we can come up with to attain pleasure, happiness, joy, etc. However, we also all have breaking points. This is where the pain we create by these behaviors, mechanisms and patterns is greater than the pleasure they provide. That’s when we’re ripe for a change. Sounds to me like you’re reaching that breaking point. Hence, you’re reaching out for help. That’s not a bad thing, that’s a good thing!

If being passive, hanging back until a guy asks you out, is causing nothing but regret and frustration, then the answer to Dr. Phil’s patented question: “How’s that workin’ for ya?” is, “like sh*t.” Time to let go of the pattern of waiting and create a new pattern of taking initiative. You’re not asking him to marry you, you’re not asking him to carry all of your emotional baggage, you’re asking if he wants to spend two hours having a couple beers or in a darkened movie theater, or on your couch watching Cowboy Be-Bop. Keep it in perspective.

Everyone’s scared of getting hurt. It’s programmed into our homo-sapien-sapien DNA. Nobody jumps in line to fall on her sword. But let’s be realistic, asking a guy out and falling on a sword, while they may sound similar, are in fact two very different types of putting yourself out there. Keep it in perspective.

Asking a guy out doesn’t banish him from your life, but does it risk awkwardness? Sure. You know what it also risks? Him saying “yes.” And if he says “no” then that doesn’t make you less worthy of dating, it just means that for one reason or another, you’re not going to go out with this guy. Still 150 million other options exist in the U.S. alone. Keep it in perspective.

Asking someone out is like any other skill, it gets easier with practice. You talk to anyone in the arts and you’ll feel better about a guy saying no to Saturday night. Those folks are in the business of constant rejection. They’re also in the business of constantly having to put themselves out there. The first time will be the hardest. But just keep it in mind that the regret of not knowing is a far more chronic pain than the sting of a rejection. The second time will be hard but you’ll have experience to draw on. Sometimes it’s easier to start by asking out someone you’re not Jonesing for. Sometimes it’s easier when it’s someone you’re just meeting and having a decent conversation with. Then, work your way up to the boys whose names you’ve been doodling hearts around all year.

The bottom line is: Yes, it’s time you started getting comfortable making the first move. Yes, it’s time you stopped letting your fear keep getting you hurt through inaction. Yes, it’s time to grow a pair and put yourself out there! Keep it in perspective, how much worse could it be than what you’re going through now? Answer: Probably none.

Always asking,

Marcus Duderelius

[Isn’t he amazeballs? Sigh, we know. Too bad he’s taken. Check out The Dude’s other insights into the male mind right here.]



  1. Steph says:

    You said Homo sapien sapien. As an anthropologist, that made me happy :)

  2. Steph says:

    Ack! It blocked out the first word! I was using it a non negative way :( now i'm sad

  3. Shelly says:

    I totally agree.I have been pining after my best friend for a year, and a few months ago, I made the decision to finally tell him how I feel. He told me he feels the same, and I got the best kiss EVER!!!
    We are a happy couple, and about to move in together!

    Moral of the story: you don't know if you don't try!!

  4. Alison says:

    you don't need to directly ask a guy out. But you need to drop hints that you like him. It's up to you how you want to do it, but you need to convey the message that you are interested in this guy. THEN if that doesn't work, you take the plunge.

  5. Maria says:

    Excellent advice. I was just like you, always pining after the guys, waiting for them to get the balls to do something, and then nothing would happen. I was so frustrated and so finally I decided to tell this guy that I had been crushing on forever how I felt. It was probably one of the scariest moments of my life, but so worth it in the end- because he was impressed at my guts. We ended up "talking" and although things didn't work out between us in the long run, it was still worth it because it has given me the courage to continue to put myself out there with guys. Remember, you never want to have to wonder "What If?"

  6. Ohhonestly says:

    Homo sapiens sapiens. Can we at least spell our own species name correctly, even if we can't italicize it properly?

  7. Sarah says:

    I'll be the annoying person that asks a question here, too similar to ask this amazeballs guy. But a very close guy friend I've just been crazy about for years (sophomore in college now, since I was a freshman in high school…ack!) Sometimes we don't talk as much or grow apart for a month or two, but then we catch up/hang out and we're back to normal. I'm more comfortable around him than with anyone. All that to say, a couple years ago I told him I liked him and he replied saying we should try dating, but it jsut didn't end up happening at the time. Now we've never talked about it again and he's had a gf since. Not sure what to do…but thinking it's been so long, now or never? Some thoughts? (God, I look desperate. I am haha.)

  8. Devin says:

    So I meet this guy named Sheng at his job at a water park.
    He was working and I think he is cute so I talked to him and he smiled at me and I stared into his eyes and he stared back he would also lean in closer to me while we were talking He would also help me into the water and check on me and ask if I am ok ;well I found out he is from Malaysia and that’s why he has an strange accent . Well I would walk around for a little and then come back and my sister said that he would stare at me and watch the side walk in till I came back and then he would talk to me again. Now I don’t know if he was nice to me just because he was working and I was a customer or because he really likes me. I plan to go back next Friday and talk to him again though what do you think? Does he like me or is he just being friendly? Thanks for any advice!!

  9. anna says:

    well.there’s this guy i’ve been in love with for the past 4 years,and am seventeen now,and am really sjy and he’s kinda shy to but yesterday i wrote a poem for him asking if he wanted to be more than freinds with me and how i wanted to know how he felt about me,i gave him the peom because i dont have that guts to do it in person and pluse he thinks am really good at wrtitng poems and stuff,but anyways after i gave him the poem i told him to read it at home and not in front of me,and on monday he is going to tell me what he thinks,do you think that was a bad idea???????????

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