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Will my strategy to ask her out work?

Tagged as: Dating<< Previous question   Next question >>
Question - (31 August 2011) 10 Answers - (Newest, 2 September 2011)
A male United States age 36-40, anonymous writes:

She's a good friend, I think we both have feeling for each other, so Im going to make the first move and ask if we could date.

Would it be fine (put yourself in her shoes) if I asked her if she had time to quickly meet up during the weekend so that I could talk to her about something important? Or would this approach potentially scuttle everything before it began?

I want to do it this way because this guarantees that she will meet me and that it forces me to go through with it. As opposed to asking her to hang out and then chickening out at the end of the night like I did two days ago...

What you think?

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A male reader, doublejack United States +, writes (2 September 2011):

OP, from what you just described it sounds like things are already headed in the right direction. You're doing just fine! She let you pay for the second dinner "date". There was more flirting. Those are clear signs of progress.

My advice is just keep it up. Keep asking her out, keep flirting with her, and most importantly keep being yourself. Many good relationships start out with two people being more friends than anything else, and things progress from there. That sounds like the path you're already on. The transition from friend to girlfriend can be very gradual, and it need not be explicitly expressed until after it has already happened.

That you work with this girl is an added complication, and ample reason to move along slowly as is the case here. I have personal experience dating coworkers (two of them - not at the same time of course... and both were within the last year). Those relationships started out basically the same way yours is going. I met them at work and had instant attraction. We became friends around the office. Then we started hanging out outside work - at lunch, group happy hours, etc. Time goes by and we get closer, the next thing I know I've got a girlfriend that I happen to work with.

Just don't get discouraged, because if this girl didn't have interest beyond friendship then I don't think things would have gotten as far as they already are!

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A reader, anonymous, writes (2 September 2011):

This is verified as being by the original poster of the question

thanks Odds and Doublejack,

the advice is good and really makes sense, but theres only one thing that bugs me. We've gone out for dinner twice already. She calls it just me and her hanging out. The first time we went out it was not date like at all. She wouldn't let me pay etc.

The second time she did let me pay, and a lot more flirting went on. The problem is she never dresses up, still treats it like just a friend thing when there is clearly sexual tension in the air. I feel like i need to make it clear that i want us to date.

Also, to complicate things further, we work together, so if i make one wrong move its not gonna be good at work, even if its two teenagers in part time jobs.

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A male reader, Odds United States +, writes (2 September 2011):

Odds agony auntDo not spell anything out explicitly in words. Chicks hate this. Don't tell her you've been thinking about things, or that you really are attracted to her, or that you want her to be your girlfriend. Don't ask for her approval for anything, simply trust that she is an adult who will know what you're doing and will signal her displeasure if she feels the need (obviously, respect her boundaries when she expresses them, but saying, "Would that be alright with you?" is unattractive, but not saying anything leaves her the option of just telling you to she's not interested).

Again, just let things happen (or seem to happen) naturally. Don't say a word or try to spell it out. Think of it this way: what's more alluring, holding her hand or asking if you could hold her hand? Gazing into her eyes, or calmly explaining that you are attracted to her? Kissing her, or asking if she would let you kiss her?

Don't say anything unusual. Just let your actions and body language do the talking. Believe me, she will get the point, and she is a grown woman capable of saying "Let's just be friends" without you prompting it.

If you absolutely feel the need to say something unusual, this is it: when you ask her to hang out, add on, "Wear something nice." This is universal girl-code for "romantic intentions," and makes you look smooth and in control.

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A male reader, doublejack United States +, writes (1 September 2011):

I find it best to avoid using the word "date" or any form of it. It makes things awkward. Girls are keenly aware of what kind of activity constitutes a date and what doesn't. If you ask a girl a question such as "I'd like to take you out, when do you have a free evening for dinner?" then you are communicating to her that you want to date her, without actually saying the word. She will know EXACTLY what you mean. It's just much more natural, and women in general will react in a more positive way when asked like that.

I would also avoid phrases like "things could work out between us". You don't want to send the message that you've already made predeterminations about anything. Women see relationships as things that need to be explored, each one progressing in its own way. You wouldn't bring up the idea of marriage on a first date, or prior to it, right? Saying things could work out is just as intimidating... it's a conclusion that can't be reached yet.

Finally, I would also not offer the easy out of "if you just want to stay friends, then that's OK, too". If she's really into you then she's of course going to accept a date offer. If, however, she's on the fence and not quite sure, she may instinctively take the easy out *if* it is offered. If she'd rather stay friends, make her suggest it as part of her declining your offer to take her out.

Hopefully this advice can help you out a little bit. Remember, there are MANY women out there... so if this girl isn't the one don't get discouraged! But you won't know until you ask her!!

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A reader, anonymous, writes (1 September 2011):

This is verified as being by the original poster of the question

thanks everyone for the answers. I'm definitely just going to ask her to hang out again and go from there. Doublejack mentioned that I should not talk about dating and being a couple.

My plan was to tell her that I've been thinking about her and that we have a lot in common etc and that things could work between us. Then ask her if she would ever consider us dating each other? Is this a bad idea? How else could I say it? I want to get my point across I don't want there to be any "i'm not sure what hes trying to say".

As well, should I also mention that if she doesn't feel the same way that I'd be glad to remain friends or should I leave that part out?

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A male reader, doublejack United States +, writes (31 August 2011):

I have to agree with the advice you've gotten to this point. Your plan is pretty formal for the times, puts pressure on you and her, and comes across as awkward and needy, and maybe even desperate. Women are much more comfortable when relationships develop in a more spontaneous and natural way. If you over emphasize a meeting and then proceed to put her on the spot like you suggest, the odds are she won't react well. Even if she likes you, she might get evasive purely as a defense mechanism. Then later on she'd say something like it isn't a good idea, or she doesn't want to ruin the friendship, etc.

My advice is to keep "hanging out" with her. Look for cues like her to say that she had a lot of fun, or if she touches you on the arm or leg (if you're seated next to her) in conversation. Those are good indications she's warming up to you and is possibly willing to see where things lead.

If you get the signs, then at the end of the evening tell her something like "I've found myself thinking about you quite a bit lately". That's a subtle and unassuming way to communicate that you like her, and she WILL pick up on it.

I like to start out as friends so I can get to know a woman first in a casual way, and if I feel there's chemistry this is how I escalate things beyond the friend zone. It works, trust me! A couple weeks ago I said that to a girl that I've known for a little over a year. We've been hanging out since December / January and became good friends over the past few months. When I said it, she admitted that she's been thinking about me a lot, too. At no point did I suggest we should "date" or say anything like "we'd make a good couple"... yet, we're definitely dating now.

Just be confident, keep it cool, and let her lead before making your move. If you do that then you'll be good!

Best of luck!

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A female reader, anonymous, writes (31 August 2011):

Why would you use the word quickly? Just ask her to meet up with you and have a coffee or something because you want to talk to her about something.

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A male reader, Odds United States +, writes (31 August 2011):

Odds agony auntIt's too formal and high-pressure. Chicks don't like pressure, and they prefer that relationship-related things "just happen," rather than being planned in advance. You're not trying to trick her, you're trying to transition a relationship.

Just ask to hang out Saturday like you normally would, go someplace with a sexual vibe - anywhere with dancing and alcohol works, but in a pinch, any physical activity where you will be in close proximity works (rock climbing, hiking, swimming if you can get some measure of privacy). Build up the fun energy, stay close to her, hold her hand or put your arm around her waist (do it like you mean it, too - no hoverhands, either go all the way or don't try), and when you make eye contact, hold it even when you get nervous. Go fo rthe kiss when the energy feels right. Treat it all as if it just happened naturally - because, if you ran things right, it really did.

Turning a female friend into a girlfriend is tough to do, but best of luck to you.

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A reader, anonymous, writes (31 August 2011):

I recommend not saying "I have something important to talk to you about." I understand the practicality of this approach, but it might make her nervous...or it might make her expect too much.

If you haven't said it yet, the chances are you're not ready to. My suggestion is to enjoy your time with her, like you already do and when the opportune moment presents itself, tell her how you feel.

Don't ask her to "can we date?" Tell her how you feel about her. That way, you're not asking a question and consequently demanding an answer out of her in the moment and she'll be more likely to respond.

This stuff is scary...even for women. I would say wait until you're ready. Don't put a due date on yourself or give yourself an assignment. Wait until it feels natural for you.

From what you say, it seems like it will go well.

Good luck.

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A female reader, xanthic United States +, writes (31 August 2011):

xanthic agony auntA quick meeting is definitely not the way to go, it would make things seem rushed and could potentially be awkward. Besides, it shouldn't be about guaranteeing she'll show up. It's better to make plans to hang out, spend some time together doing something fun that you both enjoy, then ask her towards the end. You might've chickened out the last time, but it'll be easier after a great day together than it would by meeting up and starting off the day with asking her out. It'll reflect better on you and your intentions by showing you're willing to make time for her.

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