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I'm hopeless


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I've been introduced to a "friend of a friend", lets call her X, that I think is really cute, easy to get along with, and is definitely single. I've been chatting with X online, mostly, since she lives accross town, and she has a child to take care of. Whenever we do spend time with each other (always in the company of others, so far), we get along really well.

She has expressed some amount of attraction to one of my roommates, but he is in a relationship.

Lately, I have been getting called out by a couple friends (including X's friend that introduced us), saying X has been asking questions about me.

X and I have been flirting a little bit, but I'm not sure if I'm getting all the right signs from her... combined with the fact that I know she had (might still have) an eye on my roommate.


I'm wondering if anybody has any experience in a situation like this, or any input that could put my mind at ease.


I'm not worried quite as much about rejection, as I'm completely hopeless when it comes to figuring out how to approach her.

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I feel you man, been there.


I've learned the following:

If you're wondering about her being attracted to you, or if you should kiss her and such questions, you're usually right and a step behind. your subconscious reads all kinds of subtle cues such as body language, fluctuations in tonality, eye movements..etc. now of course we don't consciously register this stuff, that would be way to much input. but we get a feeling, a hunch a gut impulse, right?


unless you're trying to talk yourself in to it and you're hypnotizing yourself, you can trust your gut feeling.


based on the facts you write in this thread, she might be in to you or she might not. its impossible to say for sure for an outsider. you on the other hand or lets say your subconscious has way more input. trust it. don't let insecure logic excuse processes mess with your head.


oh and good for you for dealing with the rejection issue. thats something that took me a long time to get over.

so if you're ok with rejection, push the interaction a bit and it will become quite obvious wether she is in to you or not.


now, she might already be in to you or she might not be. the cool thing that I've learned over the years is that you can actually influence her attraction level to you.


in short, this is what I learned:


- be playful, be fun, be outgoing, make her feel good. basically show her that you like her, but that you do not depend on her, that you are not needy or creepy.


- then once she feels comfortable and giggly around you, you can start giving her hints that you might like her. be ambiguous about it though, it keeps her curious.


- from there on have the courage to take the necessary steps to take the interaction where you want it to go. its your job as a man to lead the interaction. its her job to pace it.


I hope that helps.


don't get to wound up about it. treat it as a learning experience. have fun. experiment. don't take it to seriously.

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Thanks for the input, Amir.

I've sort of been trying to play out that first step.

Up until a while ago I would start conversation online just about every day (I chat online with a lot of friends, and she knows that, so it isn't really out of character... I think), and thought I was giving her a bit too much attention, so I stopped... didn't want to get to the point of annoying her.

Now she's the one getting ahold of me online, but it's too hard to tell what's going on in her head through the internet.


I guess I'll just play it by ear, hope I don't choke, and see what happens.


Any more advice?

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Your welcome,


Good. Especially over chat its easy to give a girl to much attention and its difficult to gauge her reaction to it. Well done.


Hm.. well there is ways of getting a girl to come all the way to your door without ever talking to her. Its been done many times.


I'm just wondering if it might not do you good to get some more practice with girls on the phone because its really all about experience. There's a couple things I could tell you to look out for on the phone but 95% comes down to feeling comfortable and in the moment. Its got a lot to do with improvising, not being outcome oriented, non-needy, fun..etc.


Try this:

Give her a short phone call but don't mention anything about a date or anything in that area. Just come up with something fun that happened recently. A story that has a couple punch lines. Tease her a bit over the phone, make up a cute nickname for her, stay playful.

Start mentioning this great event you'll be going to sometime next week, get excited about it, but never even hint that she can come along.

Then when the phone call is at a high point, end it, you have to go, your cat ate the dog or something silly.


This will leave her thinking about you in a good way and the next time you call or chat you can suggest, that she comes along to this event. (suggest, don't ask)


Even if it doesn't go exactly the way you'd like, you'll learn a lot and gain some comfort with this situation. Look at it as an experiment. Have fun with it. She'll feel it and it will go smoother for that.

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I'm not worried quite as much about rejection, as I'm completely hopeless when it comes to figuring out how to approach her.


Prepare prepare prepare. I suggest you brainstorm for a cool and fun date for both of you to have, and once you're sure that she MAY like it you can the proceed to ask her out. If she explains that she doesn't like the idea, ask her for her input on what she would rather do (of course, at this point it's safe to say she's interested in doing something; good sign!). If you are prepared with a cool idea, and are curious about her tastes, your chances of her accepting are much better than improvising in my opinion. Please, whatever you do don't overdo the brainstorming; keep the idea simple and fun. A concert perhaps?

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Hey I've been there. I used to be real shy and looked for undeniable signs that someone was into me before I attempted anything. No Mas I say, that is a bad place to be in. It looks like you have the signs. You two are flirting, you two are talking.. you two have some chemistry. Why not put yourself out there? Instead of waiting for these overwhelming signs that she likes you let her know you like her.


If you aren't afraid of rejection I don't see what it can hurt and it's not like if you do get rejected it is going to destroy your chances. The key is if you do play it off like you don't mind. Make sure things are not awkward between you two and go about your business. Do not change the way you interact with her while at the same time flirting with and looking for other girls. If you do this as Amir said ultimately it will show her that hey you like her but you do not need her.

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I've heard the "act like you want, but don't need" thing a lot... and even though I understand the concept, I can't envision myself from the other side, so I have no idea how I'm coming accross... Basically I treat her like any of my other friends, but I give her a bit of extra attention.


I gave her a call today to let her know I saw something that reminded me of something she drew a while ago, we shared a laugh, then I had to get back to driving.

Went for the "short and sweet" with no real intention, but to indirectly let her know I was thinking of her.

Should I have gone about this a different way, or not at all?


I think my biggest mental block is that I really want to get to know X better before I ask her on a real date (if this makes sense to anybody). I've met X a few times, but always in the company of others. The closest it's been to "just the two of us" was a week ago when I took a day off because the weather was supposed to be nice, and she said her and her friend had the day off too, and wanted something to do, so the four of us (X has her kid on her days off) went to a park. It was pretty casual, I'm actually pretty good friends with X's friend (the one who introduced us initially), and I think her presense psyched me out a little... felt weird giving X too much attention in her friend's company. Hope I didn't unknowingly sabotage everything on that outing.


There's my latest rant... any more advice would be great.

I'm thinking really hard lately about everything that has been said, so far my confidence has gone up (enough to give her a call out of the blue).

Thanks a ton so far, everyone.

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I agree with the "act like you want, but don't need"-mentality a lot.

If you really feel that way you don't need to worry about how you are coming accross. If you're faking this mentality, then its a different story. She might buy in to it or she might not. Girls tend to have very fine tuned radar for BS.


So really get to the point where you understand and believe, that this is not the last girl you will meet that is interested in you. Matter of fact is, that there is probably a couple more out there right now that you don't know about and after a couple more dates you'll have enough experience to spot it easier and to generate attraction quicker.


I think this point is crucial.

Back in the day I was good enough at faking confidence and smoothness that I wasn't that much worse of than I am now. What makes the big difference now is that I actually don't care that much about individual girls anymore, in the beginning that is. After that its quite the opposite.

I was able to get laid back about the topic, when I realized that girls aren't as picky as we men think, that they want to have intimacy just as much as we do and that its not a men versus women - trying to trick her in to something - thing.


Its all about the mindset.



I can understand that you want to get to know her before you make the big step.

I think you're making excuses though, because it seems scary to you and you want to make 100% sure its going to work. Your shooting yourself in the foot though. The best way to find out if this is a girl you want to date is.. by hanging out together. You don't have to think of it as a date if that makes you nervous.

I personally don't like the idea of a date anyway. It puts way to much pressure on both people.


Make a casual fun excuse to hang out with her. (get her to help you pick out a new shirt, shoes, groceries, pillow cover, birthday present for someone..etc.)


The phone call sounds good by the way. The way you describe it gives me the impression, that you handled it pretty well.


keep it up, it sounds like you're learning a lot, pushing your comfort zone and actually getting results.


good work.

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Thanks again for all the great help.

I'm trying to pay attention to everything that has been said... actually caught myself trying to think of an excuse not to go have some fun with my friends tonight, because I figured she would be online. Again, glad I realized what a stupid idea that was, had a great time out with some buddies. Why would I pass that up?


The biggest obstacle at the moment that is restricting our ability to spend time together is distance. She lives on the opposite side of the city, and with the terrible layout of the roads, it takes about an hour to get to her end of town. A little bit too -out of the way- to have a casual meeting... unless my job brings me down to her end and I have something to do right after work (which I'd also like to avoid because I doubt I'm at my best -- looks and smell -- after a long day at work, covered in dust or worse).


Amir, I do have to thank you a lot for having so much insight to share. I hope to help anybody I can when I get the opportunity.

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Thanks for the input, Amir.

I've sort of been trying to play out that first step.

Up until a while ago I would start conversation online just about every day (I chat online with a lot of friends, and she knows that, so it isn't really out of character... I think), and thought I was giving her a bit too much attention, so I stopped... didn't want to get to the point of annoying her.

Now she's the one getting ahold of me online, but it's too hard to tell what's going on in her head through the internet.


I guess I'll just play it by ear, hope I don't choke, and see what happens.


Any more advice?



you're looking good so far! why not ask her out to dinner or a movie?

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I really should just get over myself and ask, you're all right.

The distance thing really shouldn't be an issue, and actually it should help because it means I won't be able to be around her TOO much.

Only thing running through my head is her kid, now. I don't know how much time she needs to plan, or how long she can really be away.


Building up some courage, getting as many ideas run through my head.

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Criticize and suggest.


I want to give her a call either this afternoon / evening, or tomorrow, and get this next big step over with (asking her out).

My ideas: Call about something casual, mention the movie, or whatever event, midway through as it comes up... but not let it seem like it is the only reason for calling.

Also,judging off advice I've read... instead of asking her out, would something along the lines of "Thinking about checking out [bla bla movie - not sure whats out right now], you should come with me" be worth a try?

Probably carry on the original topic after that, whether she agrees or not, again, for the "want but don't need" effect.


Got a lot of thinking to do, really appreciate all your help and support thus far.




Was thinking today about what's happening this weekend, and remembered a relative of mine is having a birthday get-together, to which I'm invited.

I don't know anybody there, apart from my relative and maybe one or two of his friends.

So my idea goes as follows:

Call X, and tell her I'm in need of some new clothes, going shopping tomorrow or friday, and would like a female perspective (in my head it makes sense). Should I try to get ahold of her tonight or tomorrow (possibly last minute).

Somewhere in passing, either over the phone, or when at the store (if she agrees), the question "why do you need them?" will arise. I answer truthfully, talk up how it should be fun, etc... but don't invite her.

Depending how the rendezvous / shopping goes, tell her she should come along. Yes, great, No, at least we got some time shopping. Worst case scenario at the party, neither of us really knows anyone and at least have each other to talk to.


Any ideas or suggestions?

** Thanks again thus far!

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Went with my last idea (clothes shopping) for thursday, she said she couldn't... then said she was available friday instead.

Casual, innocent, nothing to be nervous about.

All I have to do now is be myself, right?


Would it be out of place to suggest she comes to the party on saturday if all goes well on friday?

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you're very welcome JBomb, I wish I had been able to give myself the same advice back in the days, but maybe it was good that I learned the hard way. That way it really went to the core.

But I think you'll be fine without the pain =)


If you're interested in educating yourself on the subject of dating, social dynamics and behavior in general, there's a free podcast with more then 100 hours of information and blogs at the internet address in my signature. A lot of my knowledge was gathered there.



Good for you for going out with your friends and not putting the girl on a pedestal. Girls are great, but once you make the more important then your friends and your own well doing - so to speak become desperate to please them - it blows things out of proportion. I also don't think they like it. Maybe at first, but it creeps them out quickly. Just like it would for us as men.


About the obstacle of distance:

- consider meeting some new girls, get some options. Now that you've had some success, you're feeling more confident, keep the iron hot and be social. be proactive about meeting girls everywhere. Coffee shops, the street, bars, restaurants, malls..etc.

Having options makes you a lot more laid back and you'll be able to just flow with whatever comes up. If one girl can't make it, or lives to far away or some other problem it won't phase you.


- she knows that you're interested in her. keeping it casual is not to fool her, its just so it doesn't put huge pressure on her, that she has to make it up to you. So I think at this point you can actually be quite direct about meeting up with her, because you think she's cute and you enjoy her wit, sarcasm, creativity or whatever it is you find special about this girl.

I suggest you do something different then dinner or movies. I'm not saying it can't work, but these cliche dates have a low success rate for several reasons. Be creative, be different. Do something interactive, casual if you want like going shopping together for something fun and then going to a comedy show or a bowling place..etc. I'm sure you get the picture.


So if it to far for a "casual" meet up, make it overt, go have some fun with her and see if this is a girl worth dating.


Good luck




just saw your last couple posts on the second page.


good work man! I like what I'm reading.


clothes shopping is an awesome date, great for messing around, being playful shoving each other around..etc.

I like to be as playful as possible on these first dates. I like to go in to ridiculous role playing such as that she and I are getting married, that she's going to build the house since she has such a firm handshake..etc. Its great fun, she's laughing and at the same time she starts feeling comfortable around you.


about the party:

look at it this way. if she proves herself to be fun and outgoing, tell her that you appreciate that about her and that she's invited. if she comes, great, if not, doesn't matter, you're still going to have a good time. invite her to your place to cook or something like that another time.

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I think I've got my mind in more-or-less the right spot right now.

I'm perfectly happy with my life right now, and I've made that pretty clear, I'm just letting her know that it would be fun to have somebody to share the attitude with.

I definitely don't NEED to be more than friends with her, it has potential to add something.


Really I'm just getting a bit nervous about getting tongue tied tomorrow. I keep telling myself that it should be fine, I know there's tons of stuff to talk about, I just need to keep myself focused.


I'm sure I'll post an update about how it goes, good or bad.

If its bad, I can just use it as a learning experience. No harm, no foul.



Can you tell I'm anxious? haha.


thanks again for the support, I think this forum has done wonders for me in the last week.

I've been swallowing my shyness and approaching complete randoms lately, just to let myself know that people are generally friendly, even to complete random strangers... Although I still hesitate a lot when approaching women my age.

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sounds like you have your mindset together.

I like what I'm reading.


the learning experience frame is money. definitely use that one. even if it goes well. that perspective is always valuable.


its great that your anxious. the more uncomfortable the situation, the more you will learn, the greater the relief will be when you succeed and the more you will gain self respect for doing it anyway.


big up for approaching and engaging people. great work!

I've gained so much in confidence and smoothness since I talk to almost everyone that comes within 5 feet of me. giving value to random people in turn reflects even more value back on you. its funny how that works.

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Well I'm not sure what happened there...

She had her kid, who was tired, and thus, a handful.

Things seemed pretty good, a few moments of awkward silence.

She helped me pick out some shirts, blah blah blah, joked a bunch.

That's about it... no real progression, didn't really feel anything too profound while there.

She's over here now, but so are a lot of people so it's really impersonal.

Her and her friend just ran out of the room for some girl talk.

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I called her again this morning, as I was heading out the door, just to thank her for her help last night.

Got past the formalities, she apologized for having to give the kid so much attention and getting interrupted, then told me that she'd like to give it another go when her kid is at a day home.

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5 Signs of A Strong Friendship – ...
5 Signs of A Strong Friendship – Spotting A True Friend


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