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Tips on asking a girl out, for the socially awkward guy

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What are some tips on asking a girl on an informal hey-you're-pretty-cool-let's-hang-out date? These tips should be targeted towards the socially awkward guy who, for whatever reason, hasn't had much luck asking women out in the past.

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Solution #1 submitted by venulia on Jul-2-2007
Solution #2 submitted by alexis on Jul-2-2007
Solution #3 submitted by Vito Corleone on Jul-5-2007
Solution #4 submitted by Fish on Jul-16-2007
Solution #5 submitted by jesslin on Jul-24-2007
Solution #6 submitted by Benjmonge on Aug-6-2007
Solution #7 submitted by BlowieBen on May-24-2008
How will this idea be judged? Trial by fire - I'll try the decent ones and see what happens.

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Solution Submitted on 5/24/2008 1:43:50 PM
BlowieBen submitted a solution. Click here to rate the solution or add comments.
Confidence is the key. That is easy to say, but how can you build confidence around women? I have found that it is best to condition yourself to talking to women. I don't know how confident you are, but let's say you get jittery just aproaching a woman that you don't know at all. You need to condition yourself to approaching women, so what you can try doing is simply going up to women on the street and asking them the time or directions. Eventually, you'll be absolutely fine with it.
Next step is to get used to starting a conversation. If you're out, you are now happy with approaching women, so now just aim to start a conversation, just for a minute or so. When you run out of things to say, tell her it was nice to meet her but you have to go.
So it goes on. Practice taking the conversation further (try to expand and give views on what she says, don't just ask a series of boring questions). You'll get a lot of rejections, but eventually, you won't care and you won't get nervous any more.
When you ask a girl out, I like to tell her that my friend is having a party and she should come. She says 'yes', you say 'ok, what's your number?'. This is better than just blurting out 'erm, can i have your number please?'.

BTW, this is all straight out of pick up artist - type books. There's millions out there, so it's worth giving them a read if you want to get better with the ladies.

Hope this helps, Ben.
Solution Submitted on 8/6/2007 2:55:50 AM
Benjmonge submitted a solution. Click here to rate the solution or add comments.
Get the local radio station to call her live on air and do it on your behalf. That way you don't have to worry about what to say or how to say cos they'll do all that for you. If she says yes, you're onto a winner, if she says no, too bad but you won't have to face the scenario head on if you don't want to!

Good Luck!
Solution Submitted on 7/24/2007 8:02:42 PM
jesslin submitted a solution. Click here to rate the solution or add comments.
This is kinda long, but here are some of my tips:

1. Be interested in the girl. Sounds so very simple, right? Yet, I find that a lot of guys love to drone on and on about themselves and will never ask the girl a question. Even worse is when the girl is trying to tell a story about herself, and the guy turns it back to him before she finishes. Very annoying and self-absorbed. So, find out what she likes to do, where she's from, food she likes - anything that gets her talking. If you find that she enjoys talking about a certain topic, ask more questions about it. If you can relate to anything she says, share your story, your views, etc., but try not to go off on a 20 minute tangent about yourself. Then, you'll be the perfect balance of listener and interesting conversationalist.

Also, I think this is a great strategy for someone that is socially awkward because if need be, you can let her do most of the talking. And if you are worried about an awkward silence, try to think of a question while she's talking so that after she's finished, you can seamlessly continue the flow of the conversation. This is tricky at first, because you have to listen to her and not faze out to think of the next point of conversation. But, if you get it right, it'll make you look smooth and confident.

2. If you approach a girl in a bar, you have to appear as if you have no ulterior motives. Try not to use a line. Walk up next to her and say something neutral, nothing suggesting that you might be interested, because the girl may immediately put up her defenses, assuming you're out on a mission to pick up chicks. Comment on whatever game is playing on the TV if she's watching, or whatever music is playing. Try to keep it casual.

3. Be conscious of the faces you make. Look at her eyes when she's talking to you. May feel awkward at first, but it'll show that you are interested in what she has to say. Lots of guys' eyes move towards the lips, which is very noticeable and suggestive, or even worse, the eyes dart to the boobs, which is EXTREMELY NOTICEABLE, even for a split second!! Don't think we don't see it. Just because you can't see our eyes at that moment, doesn't mean that we can't see yours.

Also, if she is telling a story and laughing about it, smile or laugh with her. It'll make her more comfortable. Try not to look too serious or intense. This can be mistaken for disapproval or condescension. A few nods, and "uh-huh"s works well to convey interest. Please use sparingly though, because too many looks like you've just zoned out.

4. Try to keep the conversation positive and light. No girl wants to date a complainer or a downer. Not fun.

Then, after you two have had a lovely, interesting conversation, you can ask her "hey, do you want to get coffee some time?" or "can i call you sometime?"

Hope this helps! Good luck!
Solution Submitted on 7/16/2007 8:52:02 AM
Fish submitted a solution. Click here to rate the solution or add comments.
Afternoon mate! Right, mainly you've just gotta be polite (everyone loves a nice guy, and NO bad language), be cheerful (a happy smile works wonders) and be confident (even if inside you feel like ya gonna cry!)

If ya trying to ask out a stranger, say in a bar or something then approach them and start up a conversation, maybe offer to buy a drink or something. Introduce yourself and let things continue from there. It's best to be friendly rather than aiming for a date straight away, seems desparate and she may be offended. Your likely to make a few girl mates this way before you strike it lucky with someone, but at least you'll become more confident around the other sex.

If you're wanting to date a friend/colleague/etc then I'd make sure that you both have a solid friendship first, let her get to know you for you and make sure you both get on well. If there's an opportunity for you both to spend time together in a social setting (work night out for instance) then try to spend alot of the time with her, see may start to see you in a different light and you'll both be really comfortable with each other. Then when you feel ready ask her if she wants to do something, just the two of you. She'll really appreciate that you spent the time getting to know her first.

Well good luck mate, let me know how it goes!!!
Added by Eilon on 7/6/2007 8:49:01 PM Rating: 2
Who wants to go out with me to the art museum at an undisclosed time?
Solution Submitted on 7/5/2007 1:13:15 PM
Vito Corleone submitted a solution. Click here to rate the solution or add comments.
Ok, now listen here don't be macho, a jerk, dont brage, dont be a man. Be a gentalman, but dont forget to also be respecting. For anything that has anything to do with dating you have to have confidence, this will come from you clothing, hair, hygene, cleanliness, your posture, and your inner self. No girl or guy likes a guy that is low in self esteam. Do stage and learn improv, i know it sounds odd but stage will help you gain self esteem and it makes you confident and improv will help you think of things to say when you are under pressure. Improv will help you greatly.
Solution Submitted on 7/2/2007 11:02:08 PM
alexis submitted a solution. Click here to rate the solution or add comments.
Be direct, do it in person, don't specify a date/time until you've gotten a yes/no response.

NOTE: These suggestions are best for an aquaintance or a stranger - they're focused on getting a "yes" to the date offer so that you have at least an hour with the person to get to know them and show them that you're worth going on a second date with.


1. Be direct - if you ask me "Would you like to get coffee with me sometime?", it's a question that says "Would you like to spend time with me?". It's direct, and I have to answer. Don't give an her an easy out (e.g. "Hey, are you free for coffee sometime?" can be answered with "Oh gosh, I'm so busy right now, I don't think so" and "Are you free this weekend?" can be answered with "No"). If she's not sure how she feels about you and she has an easy out, she'll probably take it. If there's no easy out, she may say yes just to avoid being rude and think to herself "well, who knows, could be fun". I've gone on more than one date because the guy was direct and I couldn't easily wiggle out of the offer. I ended up dating one of them for quite awhile :)

2. Do it in person - you cannot see a person's face over IM or email, or the phone. IM and email are too easy to ignore, and honestly, seem a little cowardly. Phoning is a decent backup, but there's no replacement for the brave, in-person, can-see-your-face ask out. I bet it at least doubles your odds of a "yes".

3. Don't specify a date/time - if your ask out line includes a date/time (e.g. "Want to go to the art museum this weekend?"), you've just provided the easiest wiggle out ever. She says "Oh, I'm busy this weekend", and then you're left wondering whether you should ask "Well, do you want to go another time then?". It's a little awkward, and it leaves a question up in the air of whether she's actually busy this weekend, or whether she wiggled out of your offer.
Solution Submitted on 7/2/2007 8:14:14 PM
venulia submitted a solution. Click here to rate the solution or add comments.
Ask her to do something non-threatening, like coffee (vs. dinner), during the day (vs. evening), in public (so she can run away), and make sure to nail down a time and place when you ask. otherwise, she will keep putting it off :)
Added by venulia on 7/2/2007 7:38:00 PM Rating: 0
mwahahaha