I have no idea what I should do...

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I'd really prefer to hear predominately female opinions about this.

Anyways, the main question I would like answered is... Is it possible to ask out a girl who is currently my friend, without making our friendship awkward. That is to say... if she turns me down, is it possible we can continue being friends as if nothing ever happened? I really enjoy talking to her and being around her, and I'd like to take our friendship to the next level, but I feel like there's a good possibility she might not be on the same page as far as that goes. But, I don't want to ruin our friendship. On the other hand, I don't want to sit around wondering about what could be. I want to be able to say I at least tried.

Before you draw any conclusions... let me explain a little bit about her.
She's 18, very attractive, smart, funny, and overly friendly. I feel like I should elaborate on the part about her being overly friendly.
There's another guy that likes her... and she knows he does. But she doesn't like him(even as a friend). Despite the fact that she doesn't like him, she still gave him her phone number when he asked. It's things like this that make it difficult to test the waters. If I can't get an accurate representation of her feelings based on her actions, then how do I know what to do? For example, if I asked her to go to the movies with me, she'd probably say yes even if she didn't want to for fear of hurting my feelings or something...

If you want further details, feel free to ask... if you want to give me advice, feel free... but I'm mainly interested in an answer to the question I asked up at the top. If it is possible, how should I phrase it? How should I work it into a conversation. If she IS interested in me in the same way... does it even matter that much how I word it?

One last tidbit of info... Both of us have only ever been in 1 relationship our entire lives(Or at least that's what her friend says)... So I'm going to assume that this sort of thing is probably almost as awkward for her as it is for me.

Last edited by kalantir on 14 Jun 2009, 6:37 am, edited 1 time in total.

Where do you normally see her?
Is she a coworker?
What do you talk about? Work?
Do you share a special interest?

One thought -- you probably won't get a chance to do this, but if it comes into the conversation naturally -- If she gives a guy her phone number or some similar mixed message, then turns around and tells you that she doesn't like him, maybe you could ask her how she acts when she DOES like someone.

Is that how it happened the first time? Maybe she was giving you a hint?

As for the main question, yes, it could make the friendship awkward, depending on a bunch of things. How long have you known her?

Yeah... she's a coworker.


Sometimes we talk about work, but I've been doing my best to avoid that because it doesn't seem like talking about work is going to push things in any sort of a productive direction. Sometimes we talk about music, what jobs we want to have in the future, random other things...


Yes. God. We both love god and have similar morals(although admit she's a lot better at following her morals then I am). Being around her inspires me to be a better christian.


Yeah... I think it's too late to ask about that one. If I brought it up out of the blue now she'd know exactly what I was getting at instantly.


Is that how what happened the first time? I'm not quite following anymore.


What kinds of things?


About 3 months... although I've only really started talking to her the last month or so. I do however, talk to her best friend all the time. She also works with us, but I work more directly with her best friend then with her. In fact... this warrants some further explaining...

So... I work directly with her best friend(For the sake of making this easy to read, we'll call her Nikki, and we'll call the girl I like Naomi). So anyways, since I work with Nikki on a pretty regular basis, we've talked about all sorts of things. I have admitted to her that I like Naomi, but she promised she wouldn't say anything. Now, any normal girl and I wouldn't trust that promise even for a second.(I was also not aware that they were best friends at the time) But I think Nikki is actually trustworthy and keeps her promises. I've tried to avoid talking about Naomi too much because I don't want to come across as creepy or obsessive. Now, from what I have managed to gather from her, Naomi is "Not looking to date right now". However, at the point that she mentioned this, I had barely even really met Naomi. The way I figure it, if Naomi met a guy she was interested in, she could easily change her mind about that.

If Nikki herself told you that she didn't like that other guy, that might be important.
If Noami told you, that's probably nothing.

What kinds of things?[/quote]I'm thinking of Christians I knew when I was a kid, back in the stone age.
Back then, I would have said to go slow, to pal around for a while.
Work together on some volunteer project at church or something.

If Naomi is "not looking to date right now" it's probably not a good idea to jump right in, so to speak, because unless she's REALLY into you she'll probably turn you down (as for whether things will be fine or awkward afterward, that is completely dependent on the individual so it's always going to be a chance you take).

I would recommend maybe trying to deepen the friendship first - sort of do some "non-official" dates, a.k.a. ask her to do stuff with you, but make sure it's in a very casual non-commitment way to begin with. As she gets to know you better, she might come around to dating.

If she is not looking to date at the moment, she probably has a good reason for it (she might have just come out of a bad relationship or something), but there's no reason not to get a jump start on other guys - because the "not dating" status is temporary. Just be careful as you go.

Here is a summary of a scientific study of your problem: http://www.physorg.com/news151779613.html.

I'm assuming you got their names backwards... Naomi is the girl I like. Naomi told me, but she didn't just bring it up out of the blue or anything... I was talking to her and at some point I heard her poking fun at the guy to which I responded with something like "You really don't like him much, do you?". She told me that she finds him to be kinda creepy. But since she was only responding to a question I asked, I don't really think there's anything to it.

Well, Naomi, Nikki, and I have hung out during our off hours once before... There was a little party at Naomi's place and there was probably about 10-15 people. Earlier today I got invited to go fishing with her and another coworker...

Bah... using fake names for them just seems stupid now... If the person I'm worried about ends up reading this she'll know exactly who I am and who I'm talking about... I can only hope she's really nice and chooses not to tell anyone. Please


I'll keep this in mind. I'm just worried I'll get stuck in the friend zone forever... I mean, don't get me wrong. I like being her friend. But I'd hate to think that I could have been more if I simply tried.


That's an interesting article. Thank you for sharing.

I suggest taking her to lunch. That should send the message that you are a little more interested then just a friendship but it is not as bold as taking her out to dinner. This will also allow you guys to talk more and get to know each other more. If she allows you to pay for her meal I think that would be a good sign. If she insists in going dutch (you both pay for your own) I would say that's looking more like a friendship.

PS- You should watch the movie "When Harry Met Sally"

PSS- Yes I am a female who has lived on this planet for about 39 years.

How would I go about offering to pay for her meal without it being awkward.

I'm not a girl, but I can't help myself. Maybe you could buy her a cup of coffee instead? It delivers the message along with all the same opportunities but without it being as bold as dinner or lunch. Also, it's easier to convince her to let you pay.

-"Can I buy you a cup of coffee?"

Good luck!

I'm not sure, it would really depend on what she's like, and what you're like. A guy who I was just friends with all my life told me he was in love with me 2 - 3 years ago. I'm totally not attracted to him and my reaction was something like "Well, sorry, but I don't feel the same. That's okay though, we can just stay friends." but despite all my efforts in keeping things "normal", they never really were since then.

Him making very... "not handy" comments every now and then doesn't help it. Like, not too long ago, we were on MSN and I had to refresh the bedsheets, so I told him I was gonna change the bedsheets, and he said "Made them dirty? ". Now that would be funny from someone I'm at least a BIT attracted to, but it coming from him just puts me off totally.

I get really paranoid around him now. If I'm standing in front of him and he's looking slightly down, I wonder if he's looking at my breasts. If I'm walking in front of him, I'm wondering if he's staring at my ass. I don't want to be alone in a room with him, or alone with him anywhere else for that matter, and I'll be sure to let him go first every time we have to walk up some stairs.

Anyway, ever since he told me, I just started to dislike him, but that has a lot to do with his behavior around me. I think if you would ask her out and she'd turn you down, it would definitely change things for a while, but if you act NORMAL around her like you did before, there's definitely a good chance things will go back to normal as well. So don't go flirting with her if she's turned you down, or you'll lose the friendship as well.

Do you guys go to the same church? If so you could say something like "After church do you want to go get some lunch?" (assuming you go to church in the morning ) Usually, by the fact that your asking her to lunch implies that you would be paying.

At lunch if the server asks at some point "seperate checks?" You look at the server and say "No, I've got it" or if the server doesn't asks and just brings one check at the end you need to calmly grab it as soon as the server leaves it on the table or make eye contact with the server as he/she is bringing it to the table so he/she gives it to you directly.

If your going the fast food route (dining room NO drive thru) when your in line and if she's getting out her wallet or even if she is not I'd say something like "I've got it" or "This is on me"

The tricky part is if she resists you paying for it You'll have to say something like "No really, I got it." If she is pretty imphatic about paying her own way you'll just have to let it be and in my opinion accept only a friendship. If she lets you by then that would be a sign of possibility