[ash]

Hello, my name is Ash. I’m a college student, and I’m really having a lot of trouble asking one of my closest friends out on a date. I mean first day of college and I fell for her, but I wasn’t sure whether we can even be friends. Eventually as time passed by, I got the friendship thing going on and now we talk to each other almost everyday. Over the phone, texts, msn cam chats and so on, we even hang around after college together, but we’re hardly alone. Anyway after thinking about it for weeks and weeks, I finally asked her if she would go ice-skating with me over the Easter holidays and she said yes, but I didn’t want it to be too awkward so I’ve invited her friends as well as mine. Everyone from our class basically, and most of my friends know about my feelings towards her, and they’ve been telling me to make a move on this Wednesday, as she’s not dating anyone and they sort of think that she might have a thing for me. Whereas, for me I’m really confused I mean one minute I get the feeling that she’s waiting for me to ask her out, that she’s really interested when she tells me things such as ”Sometimes I really do need you more than anything else” and the next minute it’s as if we’re just good friends. I’ve tried my best to always keep her happy, and to be honest I get sad when I see she’s having a bad time herself.
Now here is my question. What should I exactly do? I’ve waited way too long already. Should I ask her out? If yes, how? If not, then why so? I’d be really glad if I could get some help on it, I can’t stop thinking about her and I can hardly sleep because I’m way too excited about seeing her the following week after Easter.

[Ask April Masini]

Yes, you should ask her out! 😀 She obviously likes you, but you’re so worried about rejection that you’re sabotaging yourself. She accepted your invitation to go ice skating — but then you went and blew it by inviting all these other people so “it wouldn’t feel awkward”. 😳 Bad move. Why are you afraid of there possibly being some awkward moments? Awkward isn’t cancer, and you can get to know someone by having those awkward moments — BESIDES, there may NOT be awkward moments. There may be smooth sailing all the way, but the point is: You won’t know unless you step up to the plate and ask her out on a date, that you then take her on, without all your friends accompanying you.

So call her up today and ask her to dinner or a movie or bowling or hiking or some other date like event where it’s just the two of you, able to get to know each other better as romantic partners and not just friends. Go do it! You’ll be fine. 😀 And if you get a chance, let me know how it goes so I can cheer you on. 😆

[ash]

Thank you so much for the advice, I finally called her and told her that I wanted to meet her. Everything went according to the way I had planned it, because I wanted it to be special. Until I asked her. She looked a bit upset and told me that she had to leave and that she’ll talk to me later on. After getting home I had a mail waiting in my inbox from her which said,

”Ashhh;

It took me forever to think what to say…
and then i forgot exactly what i had decided on…
I didnt wanna write a massive email.. but it kind of ended up that way..

Your card was really really sweet, and it rhymed and everything!
I really wasnt expecting it… so it sort of surprised me a little

You’ve been there for me in so many ways that others have completely failed…
and i have to admit that i like you more than a friend
more than i should
and more than i planned.

But this all seems so fast and im really confused
i need some time to think..
i just need you to understand that if i said no…
its not because i dont really really like you
its because i need you, and knowing what it feels like to lose you i dont think i could do that again.
I was as bad as i have ever been and i did some stupid things =/

I dont want to ruin what we already have because youre a really great friend, and i care for you alot.

And thankyou so much for the origin of my name, it means alot to me.
Can we just be normal for a while ?

xx Im sorry; i just need some time xx
Miss you. (L)”

What now?

[MadysonBelinda]

Thats good. She seems to be a genuine girl, who takes decision calmly.. Just wait, dont show your feelings again to her, she may feel that you are very gumy type..so better wait

[Ask April Masini]

Hey, listen — you did good. You did everything right. And now, she’s the loser because she’s not interested in you as a date, but wants you just as a friend.

Well, I think it’s going to be too hard for you to be her friend because of your feelings towards her, so my very clear advice to you is to move on and not spend any more time with her. You don’t have to compromise your feelings for someone, and it’s not fair for you to give yourself to her in the ways she wants, but for her to not reciprocate in the way you want. YOUR life will be much easier and better if you start looking for other women to date who want your friendship and your romance.

I hope that helps.

[Ethan Morales]

You’re clearly overthinking it. She already likes you enough to say yes to ice-skating, and your friends sense there’s mutual interest. The problem isn’t her it’s that you’re trying to protect yourself from possible awkwardness or rejection by turning a one-on-one date into a group hangout. That dilutes the opportunity to connect with her romantically.

The advice is spot-on: ask her out on a proper, private date dinner, a movie, or something simple where it’s just the two of you. That’s how you can move from friendship to something more. Awkward moments aren’t dangerous; they’re natural, and they let you learn about each other.

Stop hesitating. Take the step to show her you like her romantically. Waiting or overthinking will only make things harder and may cost you the chance to deepen this relationship. You’ve got this.

[Natalie Noah]

This is one of those moments that tugs at your heart, isn’t it? I can feel how much you care for her, and how much you invested emotionally in this. You approached her with courage and honesty, which is honestly beautiful many people never even get to that point. You stepped out of the comfort zone of friendship, showed her your feelings, and even added that thoughtful touch with the card and the rhyme. That’s vulnerability, and it takes real bravery. You can be proud of yourself for doing that.

But her response, as sweet and heartfelt as it was, makes one thing very clear: she’s not ready to shift the relationship into romance, even though she clearly values you immensely. She likes you “more than a friend,” yes, but she’s conflicted and scared of losing the friendship and the safety that comes with it. Her need for time and space isn’t a rejection of you personally, but it is a boundary and it’s one that directly affects your ability to continue investing emotionally in her in the same way you have been.

Here’s the tough part, staying close to her as a friend while your heart is longing for more is a recipe for pain. Your feelings aren’t something you can turn off like a switch, and continuing to be around her without the romantic reciprocity you crave will only deepen your frustration and heartbreak. You deserve someone who matches your emotional investment, someone who wants the same depth of connection you do in a romantic sense. Holding onto a “maybe someday” is unfair to you and keeps you from opening your heart to someone who is fully available and excited for you.

So, as painful as it feels, the healthiest and most loving choice for yourself is to create a little distance. Protect your feelings, give yourself the space to heal, and redirect your energy toward building connections with people who can meet you where you are. This isn’t about punishing her or being resentful; it’s about honoring your own heart. When you do that, you’re making room for someone who is ready and willing to love you the way you deserve fully, openly, and without hesitation.

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