I'm asking someone out for the first time tommorrow. I have no idea what I'm doing

That’s a really good idea.

FTR, I don’t get fixated on women who simply say hello to me, and I’m extremely shy. I will admit though that some of those qualities affected me in high school, but faded quickly. I haven’t had a serious crush since (I acknowledge that I need to get out more). I’ve almost forgotten what it’s like. But enough of the sad sappy BS. Of the women I’ve had a slight interest in going out with since, I’ve asked them. All failed attempts, but it was more of a few hours, to maybe a days worth of painful agonizing, until I finally got it over with, not weeks or months. I must say, that each and every time I tried, it was a relief either way. Not only was I rejected, but I felt a bit of small pride for trying, something I never did in school. And I think it’s getting better, I dunno. There are probably a couple that I haven’t asked, but I don’t obsess about them. I think the guy you’re talking about isn’t necessarily all shy guys, but the controversial “Nice Guy”. Which I’m sure shyness plays a part in their lives. Although I’m shy, I don’t think I’m that kind of nice guy. I don’t have the experience to back it up, but I’m doubtful that I’d ever put a women on a pedestal, or bad talk them if they didn’t go out with me. If ever I get into a serious relationship (Og forbid), things have to go both ways, for me, and her, without either of us getting stepped on for personal gain. I’ve seen the “Nice Guy” in action, and I’m the total opposite of that description, IMO. Even though some of the qualities are the same. I’m still learning I guess, but I don’t think I’m the obsessed type. If you leave, I’d probably be happy. I’m an Introvert by design, obsession isn’t something I obsess about. You may have taken my post from ealier as a sign of obsession. I see it as more as temporary irrational thinking, which for me is short term, but strong and intense (but not stalkerish, just confusion). I don’t get fixated by a girl for weeks or months. I don’t think I’ve explained this well, but hey…

I think this whole thing is really cute and it makes me want to pinch your cheek!

You really should try to get this girl alone in order to ask. I was thinking that you might try to innocently walk out to your car at the same time she is leaving. Try to make it a coincidence – I know I might have been a little freaked out by someone obviously purposefully trying to get me alone, no matter how nice their intentions were.

Maybe you could start out by asking if she was doing anything on Saturday night. Even if she says she’s busy, you can say, “Oh, that’s too bad, I was hoping you’d like to go shopping and out to dinner with me. Maybe next Saturday?” If she’s not busy you can ask if she wants to hang out with you, and then explain what you were thinking about doing. I think it’s a little better if you don’t phrase it as a “date.” You don’t sound like you know her at all well, and you can’t really have romantic feelings for her. Maybe it would be better to test the waters a little.

Sounds like you are a little frustrated. It does suck when you have finally made up your mind to be brave and then have to wait! Hang in there, and we want updates!

Don’t ask people out on dates – ask them to have a cup of coffee or see a flick, the same way you would ask any friend. Get to know them through casual conversation – I find, anyway, is that dating just sort of happens (or doesn’t) after just going to really casual meeting together.

It’s semantics, I suppose – it’s a date but you don’t call it a date (not out loud, anyway). When you think “date”, you probably think “OMG pressure!!! WTF do I do???” – take away that word “date”, and think of it as just another meeting, a chance to really get to know someone. If both people are interested, the idea usually comes naturally – when the time is right, you’ll likely be able to tell how you feel. Not easy, by any means, but it should feel good, never forced. (If you have to force the question, that’s really, really bad news.

Anyway, just my opinion from experience. I never really “asked out” my wonderful girlfriend. I invited her to coffee, beer, lunch, etc. the same way I would a high school buddy. We met several times casually, and then suddenly things just sorta happened.

Good luck, and stay cool – that’s most important.

That’s a good way to find yourself in “just friends” country. Whatever you ask her to, make sure that there’s someway it can lead to hooking up. I’m terrible at “dating” until I have at least made out with a girl for the first time.

We’ve got one a few miles away, but it’s gone to the dogs over the years. It’s not a very attractive place now. The skatepark section of the place is what makes the money.

Haha. Don’t worry, I have enough sense not to bring either up. I’m just saying, the Emploee of the Month thing is a credential and proves I’m good for something, and Men are from Mars Women are from Venus has dished out a few good tips. I am taking that particualr book with a lot of salt though.

Hmmm. After you said no to the persons proposition, did you leave any clues you would have been interested in meeting up later? I don’t want to blow any chances by giving up at the wrong time, but I’m not wanting to sound desperate. Looks like their’s an invisisble line between desperate and charmingly persistent. Sounds like I’m taking a risk either way. I could think about this all night…hmm…better get my thinking hat.

The Christmas shopping idea does sound pretty good. Money is short, so I’m not sure how I’d fit that in with a dinner invitation, which is something I’d still like to do at some degree…not sure why, maybe I’m just being stubborn about that. Still, I do need to get my Christmas shopping done. I could use a women’s perspective for one or two gifts.

Oh c’mon now. I may be obsessed, a little neurotic, and willing to drive half an hour just to ask a guy a few questions, but I haven’t done anything to violate this girl’s privacy or comfort. I’m a stand up guy.

All these compliments are going to start going to my head and make me uppity. Next thing you know I’ll be wearing a top hat, drinking oriental tea, and will have an eyepiece :slight_smile: .

I’m still trying to work out how to get this girl alone. Waiting outside could take hours, and would probably attract a lot of attention. I’m not wanting everyone to know I want to ask this woman out before she does, and I’d probably have to explain to more than a few people why I’m standing outside the store. Plus, I think she may find that creepy. Actually, I think I would feel creepy doing that.

Having to wait wasn’t too bad, but to get guilt tripped because half of my department called in sick immediatley afterwords just drove me up the wall.

I think she’ll get the point I’m interested in her if I invite her to eating out someplace, and I won’t have to use the word “date” to get my message across.

IIRC, the three-times rule is advocated by Miss Manners. If she really is busy all three times, she should get the hint and say something that will let you ask a fourth time: “Oh, I’m completely swamped this weekend, can we do something next week?”

One that I’ve found is pretty effective if I get an “I’m busy” response, is to say “Well, maybe another time, then.” This lets her give the very equivocal answer of “maybe,” which can mean “maybe” or “no,” or if she’s really interested, she’ll say something like: “Yeah, I’d really like that.” That way you can get the “yes” answer without asking her on a generic “date” (a bad idea, as others have said) even when she’s busy for what you asked.

Excellent idea – but, FTR, “maybe” means “no” – there usually isn’t any “maybe” in the woman’s mind. If there is any “maybe” action on her part, it will be discernible in the warmth of the “yes.” “Yeah, okay” means “maybe,” and “Definitely, I’d really like that” means “yes.”

twicks, SWF

But that’s just it – just about any activity can lead to hooking up! It all starts with casual meetings and grows from there. You ask for more than friendship when the time is right, that’s the point I’m trying to make.

Also, remaining “just friends” is something you have to be prepared for – if in your mind you can handle and enjoy “just friends”, then your mentality is in such a state that you vastly increase your chances of hooking up.

I’ve waited a long time to use this quote in a conversation:

I’m a girl with a lot of somewhat socially ackward friends that spend a lot of time being ignored or rejected by girls.

Asking her out is a great first step. If only I could get my friends to understand that staring at, watching, and following girls won’t get them dates. The only way to get to know a girl is to have some good face-to-face interaction.

That said, a full-blown date of dinner and all kinds of stuff from a relative stranger would probably freak me out a bit. I’d guess that he didn’t have much experience with girls and wonder if the guy had some wierd old fashioned ideas about relationships or something. I’d feel like this guy was expecting a lot from me and I know I’d most likely not be the girl he had built me up in his mind to be.

Most relationships don’t start in formal date situations- they emerge from friendships and social circles. If you don’t have the advantage of a wide social circle, your going to have to learn to make friends with girls. Girls don’t want a handsome prince that will whisk them off to a fancy restraunt and open doors and pick up every tab. They want someone who is compatable with them.

I strongly advice asking her to join you for coffee one day after work- every relationship I’ve ever had has started in a coffee house. It is casual and “normal” enough that you can ask a relative stranger out to it without setting off alarm bells. But it is also pretty clearly a date, and the girl will understand that you are interested in her. It gives you a chance to get to know each other. It is a short enough that the girl has a comfortable escape route, but if things are going well it leaves open the option to walk around town or watch a movie or make out in a dark alleyway afterwards.

Remember that picking a place to go isn’t about what activities interest you, but what activities the 2 of you might use as an icebreaker. You may not like playing pool, but it can be a good chance to get to know each other. The playing pool part is just an excuse to have something to do besides stare at each other while trying to come up with the next bit of conversation. That’s why pool or a walk or visiting the zoo can be more casual/relaxing then going out to dinner.

And you have to love pool when she has to play from the middle of the table to make the cut into the corner pocket and you can casually say to her, “just throw your leg up on the rail,” to help her get in position.

Gotta love hating those people who think that “18 and single” is odd…

Like AwSnappity already mentioned, if you find yourself having to draw out every line, she’s not for you. My married bro claims he knew he wanted to spend the rest of his life with Judi within half an hour of meeting her; I haven’t been so lucky but it’s never taken me more than an hour to figure out “I don’t want to spend the rest of my life with this guy”.

The Christmas show sounds like a cool thing and it’s something that you don’t have available at any time, so that’s extra points. What time is the show? I’m a day person myself, so I prefer afternoon entertainment.

Another piece of advice: always believe what your girl says over anything a book says. Some women do mean exactly what they say, and in exactly the same way a guy would say it, and I’ve found this to be especially true of introverts. We find it hard to open our mouths, so when we do, the idea is to get info across ASAP. And I also know some men from Venus…
Oh, and if she’s an introvert (probably, or her boss would have known something), remember that like you she can be enjoying herself even if she’s not bouncing up and down. Major source of Disbelieving Boyfriends for me, that one.

Errol Flynn, who was famous for his successes with women.

*[wheezy old fart voice]*Kids today. They don’t how good they got it. Why, when I was young, if a woman stood downwind of you, her reputation was lost and you had to get engaged! And skinning a possum together was considered a formal proposition of marriage. [/wheezy old fart voice]

Seriously, don’t over-analyze this. Ask her twice. If she declines twice without a counter-offer, move on. Even if she does, it starts to get the word out that you are available. And you know how those women talk to each other.

Of course, keep in mind that you are receiving advice from someone who hasn’t gone on a first date for twenty-five years.

Regards,
Shodan

Summon your courage, take a deep breath, walk up to her and say "I think you’re really nice and very cute too. Would you like to go “insert activity” here with me this Friday? When she says she’d love to, say thank you, can I have your number and I’ll call to get directions and give you a time to be ready.

An activity is good - no perfect conversation needed.

Learn table manners - find someone older or that you admire, quietly ask them if they will come to your house or come for dinner with you and help. In my dating years, I dated men who has excellent table manners and dated some guys with none. I didn’t date the guys with none more than once! You don’t have to be Mr. Manners but not slurping your soup, not chewing with your mouth open and knowing how to order are things you should know. Would be useful later in business and/or life in general.

You’ll do great!!! Be charming, listen and always look like you know what you’re doing and are in control.

Dammit, where were you all and were was the Dope (come to think of it, the Internet too…) when I was 18 and single and standing exactly in Joe’s shoes??

This is all good advice.

The only other advice I would have given my then-self, is to remember that she’s a person, not some mysterious alien from the planet of nubile cheerleaders, not some terrifying monster, nor a medieval maiden to be put on a pedestal and secretely worshipped from afar until you can prove your undying devotion by facing down a mortal danger single-handedly. A person, just like *you * are a person. A person who has likes and dislikes just like you do. Who has good days and bad days, things that tick her off, aspirations and hopes and dreams, just like you do. A person.

Think of her as in interesting person, whom you would like to get to know better. It will help you get the nervousness under control, and it will help you in talking to her.

I second the idea about not referring to your outing as a “date” quite yet. Just keep it casual.

Miscellaneous advice for guys on going shopping with a “lady of interest”:

The Christmas shopping idea is a great one. Be prepared to stifle your male boredom if cosmetics or clothing for her are involved; if so, *make * yourself interested. DO provide thoughtfull comments. Remember, *she * always looks great, it’s the *clothes’ * fault if they don’t suit her. If you’re really unsure about making any comments, touch the clothes and comment on how nice the fabric feels. Tell her she deserves clothes that *feel * great. If you do go, have at least one or two gifts in mind to get; ask her for help picking out gifts for female family members, but preferably not your mom. Sister would be perfect. The idea of buying a toy to donate to charity is fantastic, as it will make you appear nurturing and caring. Going into a CD & DVD store together is a great way of exploring each other’s likes / dislikes. The mobbed circus-like feell to malls these days can provide some sense of "shared adversity’ that can bring you two closer.

You’ll do great. Just remember she’s a person

And keep us posted.

If you’re worried about your co-workers overhearing (which is understandable), How about when you get your break, you go by the bakery and ask her if she’d mind helping you decide on a gift for your sister/cousin/bestfriend’s girlfriend’s stepsister. You know cause she’s a fellow female in the same age range, etc. Then you could ask when her break is or when she gets off work so you could discuss it off the clock.
That will give you soemthing specific to talk about and should be enough time to figure out if she’s capable of stringing two sentences together and then take your plan from there. That could even lead into going Christmas shopping together and maybe to the Village after to listen to music.

Good luck!

So tomorrow’s when you ask, eh? Keep us up to date.

Oh, and let me throw a bit of advice into this post so it’s not completely worthless. Don’t worry about it; in fact, the less you think about it, the easier it will be. Also, go in expecting “no” as an answer, that way you hopefully won’t be too disappointed.

It’s quite possible (likely, even) that her boss just didn’t feel comfortable sharing information about this woman with some random guy. I would be so pissed if any boss of mine, past or present, shared any personal information about me with anyone who asked.

Also, about the best way to get away from coworkers when you ask her out? How about, “Hey, can I talk to you for a second?” Simple and not nearly as creepy as some of the other advice (follow her to her car?).

You should never, ever ask a girl out (not the first time, anyway) today for a date tonight. Two or three days is probably enough notice. Don’t compliment her on her looks while you’re asking her out. Umm… yeah. You seem perfectly nice, just relax and have fun. Good luck. :slight_smile: