Best way to ask her out without putting her on the spot...

[Tired]

I can admit i'm scared...my two fears, public speaking and rejection. I think that's about it.

Anyway, it's a co-worker (i kno some of you will say don't bother...but its a great match imo and it won't mess up anything at work)

I see her maybe 10 minutes a day and that's about it but we've been talking for months so we know each other pretty well by now. She was shy and has since opened up to me and I can tell shes comfortable with me now but i'm not SURE she would date me as we work together and shes a good deal older than i am.

I wanna tell her that I wanna see her but its like i'm at a stand still...I don't know what to do, I have no problem talking with her but I can't blurt THAT question out. I like seeing her so much and don't want things to be awkward.

I already know shes single, i've asked if shes been married, had kids, etc...I've asked her everything I can ask pretty much and all of her answers are correct

When do girls get uncomfortable, I've had girls come on to me before that I wasn't interested in and its kinda hard to turn someone away. Advice?

[GrkScorp]

Advice?

O.K.

first of all, you're showing symptoms of "one-itis".. this is the first thing I want you to do.. give this some thought.. SHE has no idea how you feel.. (unless you seemed really excited everytime you talk.. and jumped for joy after you found out she was single).. so.. that being said.. you don't really know much about her.. there are three trillion reasons why she may NOT be right for you.. so don't feel that this is the love of your life and a match made in heaven.. why? because it will mess up your interaction with her.. and make you look less desireable..

Tips: the best tip I can offer to get over this is hang out with better-looking women.. but when that's not an option.. just talk to women.. casually.. with no intention other than talking to them.. this will make you more relaxed.. secondly.. buy a copy of Maxim.. look at the women in there, which are more than likely better-looking than her.. don't flip the page.. just look.. look.. look.. keep looking.. until you get tired and bored of what you see.. nothing special.. a pair of nice breasts, a firm toned body, with nice hips, a round butt, flawless photoedited skin, and a pretty face.. so what? big deal.. I want you to flip through that magazine and do the same thing for all the girls in that magazine.. RIDE THAT WAVE.. feel that.. you have a tolerance for good-looking women.. they're nothing special.. on top of that, may I recommend beta-blockers; you can get them over-the-counter.. they help with stage-fright by blocking the release of (adrenaline) which makes you nervous.. so beta-blockers, along with tolerance for interaction with women.. will prevent you looking like a nervous wreck when talking to her.. (that's my main concern, because you seem like a smart keen guy, the only problem I see is your fear, which is easy to take care of.. so relax ; P)

now, aside from the "fear" you feel.. guys have this horrible habbit of "rushing" things.. as a guy, you often want fast results.. NOW! take a minute to realize that this will make her uncomfortable.. and make you look desperate.. this is obviously a big no-no.. you want a smooth transition..

realize.. that she's going to work with you.. she's not going anywhere for the next two weeks.. BUT! she CAN meet someone else.. so what do you have to do? ask her out? yes.. eventually..

it's great that the two of you are comfortable.. but now you have to start hitting her with teasing/playful statements (that suggest that you're not interested in her).. this will act as to tap into her comfort zone with you.. and make you more interesting.. (haha, oh wow, does my nose or hair really look that bad? why doesn't he like me? alot of guys like me, why not him? i'll see what I can do about this).. what are some examples of such statements?

You: Laundry day today? You sure that's not you? What smells like that then?

You: You have something in your teeth, I can't see it anymore, I think it's gone.

Stuff like that makes her concious about herself.. and it's clearly NOT flirting or an effort on your part to flatter her (which would suggest interest).. but it still means you notice her.. so you seem like a challenge.. which is sexy.. that's what you want to be.. the interesting guy at work that she doesn't know if he's interested in her or not.. you DON'T want to be that guy at work who has a crush on her.. because that will just lead to her avoiding you..

Do this routine for the next week or two.. this helps to build up comfort.. because after all, your statements will get more aggressive, but she'll know you're just teasing her (example: Didn't you wear those shoes yesterday? How rare, a woman with one pair of shoes! :smile.. you know she's hooked when she starts using statements that suggest comfort to respond back.. "Oh shut up.. haha" or "very funny" or "haha, no, I have more shoes, I just like these"..

Warning: at this point you should have sparked her curiosity.. now she'll want to test you to see if you're any interesting.. most women do this automatically, but alot also calculate it.. so watch out.. and don't be NICE, be interesting.. here are some tests..

Her: Haha, no, I have more shoes, I just like these, they're cute, I think they're adorable..
You: (don't be a wimp and say something like, oh yeah, they're pretty cute, I like them too, they look good on you, anything looks good on you, marry me).. instead, try something like "I think that's really nice of you, to hang around blind people, but don't always trust their fashion advice :smile:"..

Stuff like that.. that's a "hoop" she just set up in front of you.. and wanted to test to see if you're a good doggie and would jump over that hoop to make her happy.. she would then throw you a bone "A smile, a thanks, a you're so sweet".. and that's all you would get.. but not you.. oh no.. you're not going to jump those hoops.. you're going to show her that you're not out there to "please" her and "flatter" her.. that's NOT what you need to do to attract women.. you have to have this attitude that "I don't need to be nice to women to attract them" in the back of your mind.. this will radiate the image that your a high quality male.. and people like to be with high quality people..

Good! if you do this.. she'll be thinking (ok, wow, why doesn't he like me? it's not working, why?).. this will knock her off her high pedestle and bring her to your level.. at least in her mind.. so now she will respect you as a high quality man.. and demand your attention.. and seek your validation.. it's HER that's going to be trying to PROVE herself to YOU.. not the other way around.. this is how "attraction" begins.. and this is what you want BEFORE YOU ASK HER TO COME OUT WITH YOU..

Look out for her indicators of interest.. (smiling at you, finding reasons to talk to you, keeps the conversation going, finds reasons to be next to you (0-8feet away), touches you supposedly playfully "note: you give her perfect excuses to do this with teasing comments that allow her to hit you back playfully").. so why look out for IOIs? because you want to know first.. this gives you the informational advantage.. which gives you a sense of security that "hey, I know she likes me".. what you DON'T want to do.. is feed her back IOIs.. because this will kill the tension.. and take away from the attraction she feels for you..

Once you start getting IOIs, don't look like an idiot and feed her the most common male IOI (the dumb I love you smile).. you can smile, but make sure it's a casual fun, this-is-generally-how-I-am kind of smile.. when you start getting IOIs, you have to PUMP-UP that level of attraction, to sort of seal-the-deal.. you have to come off as (interesting, fun, funny, energetic (not gay), driven, goal-oriented, passionate, the leader of the pack amung the guys, and well-liked amung women in the office).. "Read some of my other posts to see why"

After you can almost feel the tension (can't take too long).. start finding reasons to give her IOIs.. make her work for them.. it has to be stuff about her (non-physically).. "because women know they are going to age and get ugly, so they need to feel a sense of security that you are attracted to something non-physical about them".. It could be her "energy, positive attitude, she's fun, happy, nice to other people, hardworking, driven, etc".. hit her back with something along the lines of:

You: I think, it's really rare to see people who are genuinely good to other people and care about how others feel..
Her: (she's going to take the bait, remember, at this point, she's desperate for your validation) blah blah blah.. story about her that conveys that she cares about other people.. blah blah
You: Wow, that's amazing, you've just gained like a whole new level of respect in my eyes.. that's really good to know (her name).. it's good to know there're people out there like that.. because you have no idea how rare that is.. blah blah..

O.K. enough with the IOIs and the attraction game.. now it's time to get serious.. but as always "not too serious".. before I go on to the dating transition; READ THE FOLLOWING CAREFULLY!

Female Psychology: (Probable Cause): women will do anything to avoid a situation where they feel like THEY are the CAUSE & REASON for something taking place, especially when it is negative, romantic, or sexual.. this is why women want a MAN who is a LEADER, so they can blame HIM for "initiating or creating" a romantic, sexual, or negative situation.. some examples (some playful, others serious)

- Women prefer it if a man can drive, that way, if they get lost, they can blame it on him.
- Women prefer it if a man leads and takes control of a conversation, that way, if the conversation turns out to be boring, it'll be HIS fault.
- Women prefer to be "asked" and not have to "ask" for sexual encounters.. but "indirectly".. with a "probable cause" that would make is seem innocent. (example: "Do you wanna come upstairs for a second, I want to show you my tropical fish?" is prefered in place of "Do you wanna come upstairs and have sex?") In either case, a woman may WANT to have sex, but won't say it, she'll wait for the man to initiate, that way if she changes her mind, she can blame the whole thing on HIM, and, she doesn't feel like a "slut" for accepting on obvious sexual invitation.. she wants to be able to narrate it to herself as "he called me over to see his tropical fish, and well.. one thing led to an other, and we ended up having sex".. even though she knew excatly why she was going to your place.. and it had NOTHING to do with your stupid tropical fish, she hates fish!

[GrkScorp]

I can tell shes comfortable with me now but i'm not SURE she would date me as we work together and shes a good deal older than i am

Hmm.. I just read this again..

well.. first of all, throw that age issue asside with the following playful dialog one day..

Her: How old are you?
You: Take a wild guess.. I usually get anywhere from 55-8
Her: Haha, I don't know, i'd have to say (###)
You: Wow, that was pretty close, is your idea of "close" means (##) years off.. i'm actually (###)
Her: Wow, you're like a baby (or, you're so young, I thought you were older)..
You: Yeah, I noticed, poor you.. take a minute to get over this age thing.. i'll wait..

Now, you just have to keep doing what you have to do to keep her interested and attracted to you.. only then can you even bother transitioning into dating.. before that.. it's too early.. and you're making her say (yes or no, based on limited feelings of attraction, why do that to yourself and not take the 1-2 weeks to build up enough attraction?) It could be the difference between you getting the date, or staying friends.. so it's time well-worth being spent BEFORE you transition..

That being said.. your transition into dating has to flow smoothly if she's a co-worker.. she doesn't want to narrate the story to herself "he asked me to go for lunch after work, or for dinner during the weekend, and I said yes".. that won't sit well with her.. so what to do? "Be subtle, and keep the innocent appearance, which is nothing more than the excuse.. that she more than knows.."

Perfect transition in your case: (after you've preformed everything else that is) "We're all going out tonight to (name something she'd be mildly interested in.. don't go all-out.. something simple).. I just wanted to know if you'd want to come so I can know ahead of time to keep an extra seat".. (is it a date? no! multiple people, friendly meeting, clearly not intimate, no pressure, nothing to make her uncomfortable, so her gaurd is down)..

You go to the place, pick some place quiet, if it's a game.. make sure everyone knows you're going to eat someplace quiet after the game.. the point is to talk to her.. and slowly feed her some more IOIs that night.. (your legitimate reason should be that you got to so the REAL HER outside the office, and you like the kind of person she is, you like that side to her).. get her number.. tell her that you're planning to go to (something fun) next weekend, "I think you'd love it! it's totally you..".. get her number to call her.. and then don't call her for a day or two.. control yourself.. seriously.. you have better things to do..

When you reach to this point.. repost.. and we'll take it from there.. one step at a time.. lol.. best of luck..

[Tired]

her and i didn't just meet.....we've worked together for a year, been talking for like 7 or 8 months, but for me it wasn't like a love/lust at first sight. Once we started talking and I got to know her is when I started developing feelings....and yes, i'd say i'm at that one-itis stage right now.

She's relatively shy but she's actually the one who brought up the age difference, she told me her age when I was asking if she was married. A few weeks later she asked me how old I was. Most of the relationship type discussions I have initiated, I'd consider myself the more aggressive.

I don't get nervous around her, or talking to her...I feel comfy with her just not comfy enough to ask her out so far.

SHE has no idea how you feel
Unless she's naive or completely unexperienced or lost, idk...she HAS to know I'm interested. Theres no doubt in my mind she knows, she probably doesn't know to what extent. Maybe shes doubtful though, maybe she looks for reasons to believe I'm uninterested.

I know a lot about her...her family, her birthplace, her age, what she's into (hobbies), what she went to school for, whenever she goes on vacation or out of town (back home) she tells me, her dog, she admitted to me she was shy

It's just weird man its like one day or a few days she's very flirtatious, she seems so excited to be there with me, and then one day its like shes in a rush and harder to talk to. I think we're both getting frustrated a little bit with how long this is taking maybe.

[GrkScorp]

haha.. (not patronizing).. but after 1 year of working with someone, and 7-8 months of talking.. i'd say.. i'm glad you're not nervous around her.. that's a relief..

O.K. then.. it seems that you're at the stage where you need to work on (attraction).. and then.. (boost that attraction)..

since she knows you.. and you've more than established comfort.. you're going to need to walk through comfort.. and let it be the path to attraction.. you're going to use her familiarity and sense of security and comfort with you to base attraction off of.. how?

(she has some idea you like her?) great.. for her.. NOT for you.. the best way to win her over now.. is NOT FOCUS ON HER! (remember when that girl you liked started talking to other guys? worse, when she would talk about other guys to you?) be fun, lively, and flirty with other women in the office.. you want to give other women in the office as much attention as possible.. and your goal is to actually let them warm up to you, be nice to you, and like you.. (how is this going to help you? just wait and listen)..

your "target", is not going to be the object of any of this attention.. (you're going to be this almost "hero" of the office in a way.. the guy all women talk to, like, and maybe appear to want to be with.. but none of that attention is going to be going to her at all).. this is going to drive her nuts.. but more importantly.. she's going to want your attention.. she's going to seek your validation.. and in effect (her small feelings of interest in you will be magnified).. what she feels as "ehh.. he's ok.." small feelings of interest.. will turn into much larger feelings of attraction..

the office setting is the ideal setting to use this.. (you don't have to worry about "opening", everyone knows you.. but you DO have to worry about people talking.. which is why you should focus on everyone else BUT her.. this way.. not only won't SHE see it.. but nobody else will see it, which means, less likely to wind up in her ears..)

basically.. you want to present yourself as a high-value person.. someone people want to be with.. someone who is fun.. funny.. makes everyone feel great.. and again.. everyone (guys and girls) wants to be with.. it's great for business.. and it's also great for getting her attention and makeing her want your attention..

she's going to be testing you (maybe after 7-8 months) you've already been a blind victim of such tests..

Her: I can't talk right now, i'm really busy, I have to go.
You: (waits to see if you're going to not care, or if you're going to ask questions, try to start up small talk to keep her talking, basically seeing if you're interested)

Her: Is it a big deal if you can get me/do (something)?
You: (waits to see if you'll do it.. or at least to what extent and how fast you'll offer to help.. again she wants to see if you're interested)

Her: Hey you! I love that (thing you're wearing)..
You: (waits to see how you're going to react, again, wants to see if you're interested or if you're smitten by her; this test is a deal-breaker.. because if she feels in CONTROL, you're less interesting and attractive in her eyes)

So what to do? I know it's been 7-8 years.. but i'm going to take your word on it that it's been only recently since this one-itis hit..

So.. game-plan..

1. Raise your social value around the office (be fun & funny, be a great person to be around, make people want to be around you, be creative, and stroke the ego of the guys (that works for guys, if you make them feel good, they'll naturally like you), and give genuine little compliments to women in the office except for your "target" (this will show them that you care for the things they do, or how they take care of themselves, or their taste in clothes, etc)

2. Go back to my other post and get ideas on how to (neg) her.. you want her to be under the impression that everyone else can get your attention.. but you don't react as strongly to her.. PLUS, you don't want to make her feel like she's in control.. in fact.. you want to make her feel she has ZERO control over you.. she has no grip over you.. her games aren't going to work on you, you're immune..

3. After you've built up enough tension.. go and arrange a party or something after business-hours for people to come to.. call everyone else first.. do this a two weeks in advance.. and casually mention it to her (1 week before it's going to be).. it's going to give her mixed feelings.. but the feeling you're aiming for is the feeling in her mind of "omg! he invited me!".. don't forget, all this time you've been making her thirsty for your attention.. you can spice this up just a little by your delivery.. "Hey, I just wanted to let you know, that we're all going to (place) on (day).. only since everyone insisted I tell you, :laugh:, i'm just kidding, you should come :smile:" (if you've built up enough of a social "proof" for yourself, there's almost no way she can reject)

4. It's not a date, it's a transition.. the point of all this is to get her out of that office setting.. have her reach an other comfort zone with you.. and start to get to know her.. yes.. everyone is going to be talking.. but you want to slowly now drift to her and tone down your disinterested act.. you have her just where you want if she chose to come out at this point.. but don't rush.. take your time to get to know her a little better.. talk about vague concepts like her horoscope, her plans for the future, what she expects out of life, what plans she would have for her family, etc.. start to appreciate things about her, and let her know that.. (you have to be sending those IOIs back to her slowly.. and legitimize why you're interested in her.. don't be direct.. just keep it at that..)..

5. next time you see her, in the office or whatever.. and you're feeling hungry.. or you feel she's feeling hungry.. whatever.. ask her.. correction (men don't ask, they TELL).. so tell her.. "hey.. have plans for tonight? I wanna take you to this (blah blah); mostly because that's what I feel like eating tonight, but I think you'll like it too" (I know you're thinking of this moment now, but don't fast-foward to this step! it takes time to get here, so take the journey, you'll get here, relax).. make sure she has no plans for that night.. the trick (secret if you prefer) to this working is NOT so much in what you say, though context is still important.. but the DELIVERY matters more.. usually when you know you're asking someone out on a date.. your tone of voice softens, your voice almost sounds dramatic from a romantic movie or something.. (cut that crap out).. if you do this.. you're going to get a "Aww, thanks, but I actually (have to make some excuse on the spot that i'm going to feed you because I don't even know why really, I just feel uncomfortable, and this is going to ruin everything that could have happened between us, so i'll never be able to talk to you the same way after this).. sorry".. we both don't want that to happen.. so just realize.. all you're doing is going to get lunch.. that's actually all you're doing.. so relax.. it's NOT a date.. it's lunch.. so it's no big deal..

6. if you deliver it correctly.. she's going to say yes.. and feel reserved and nervous.. (don't feel like oh, she's not giving me IOIs anymore).. her body and mind are on lock-down.. she has her pocker-face on and doesn't want to make a bad impression (this is infact an IOI).. plus.. think about it.. you asked her to just come and have dinner or lunch or something with you, because you asked everyone else and don't feel like eating alone.. you just want some company.. blah blah.. no big deal, no pressure.. BUT, she DID already say yes.. so no reason to be nervous.. but no reason to be cocky either.. this is the time the two of you have alone.. to just talk.. and exchange some more IOIs.. MOSTLY YOU giving her IOIs that are legitimized..

WRONG: I love your eyes, I never noticed how amazing they look..
CORRECT: (refering to something she said in the conversation).. :be in awe about it:.. you just gained a whole new level of respect.. wow, that's amazing.. being (caring, hardworking, other positive quality, etc) is so rare these days.. but I think that just fits into what makes you who you are..

towards the end of the night.. or even better during the climax of your conversation if you set up a good friendly, fun, up-beat mood.. get her number.. (why?).. not so you can post it up on your fridge.. but so you can call her sometime.. on the weekend maybe? you're doing something on the weekend maybe? what's that?!? it's something you think she'd enjoy, or you want her to come to because it's something she's talked about? (that shows you were listening, and that you care!).. why wouldn't she give you her number if THAT's why you want it.. (the biggest mistake guys do with asking for a woman's number is saying something vague like "so, let me get your number and we'll.. yeah.. i'll call you".. that's nice.. if you're in HS or in a bar.. but it helps if you have a reason as to why you asked.. or else it just seems like.. you want her number first, and THEN you'll think of a reason as to why you wanted it)..

O.K.. I think i've given you enough to work with.. now go to work.. and start making it happen, step-by-step.. let us know when you get her number..

[Mathias]

This whole thread is tl;dr.