Need to try something new and different, any advice?

[Cyne]

Hi There,

 

Basically, all ladies I know, whether at work or elsewhere, are either taken or not my type. I've been trying to turn a new leaf and try something new, but when it comes to this subject matter, I'm not very creative. I'm a guy in my mid-20's and interested in women around the same age range, 20-29 typically. Last person I dated was last July and sadly only lasted about a month (a good friend had set us up) because she just wasn't my type. Before that, 3-4 years prior, same thing - lasted less than a month, same reasons to be honest. I don't seem to get chances to run into and start up any form of attraction/flirting/dating with women, I suppose it's my bad luck with the dating scene I've always seemed to have.

 

On another note, there was on girl I met a couple weeks ago at a restaurant (she was my server) and there was something about her and her personality that I really liked, not something I see in a woman very often. I felt compelled to write her a kind of 'secret admirer' letter, but I haven't decided on whether I should or not (it feels a bit immature and/or stalker-ish to me). I also really wouldn't have a chance to watch her read it and gauge her reaction. I'm at a loss at the moment, anyone have any thoughts/suggestions?

 

Cheers!

[BiCurious2011]

Some people always say bars or clubs are a good place to meet women...I've not had any real success there but I suppose that's something you could try. If you're a church-goer, you could meet women at church. Even if you're not, you might go to meet girls.

 

As far as this server you were talking about...you could try to go to the restaurant sometime when they're not busy and hope she's working. Try to strike up a conversation with her or something, and see where things go from there. Also this might sound lame but you could try to ask a friend of yours to talk to her for you. Try to find out if she's available or not, and if she might be interested in you. It might embarrass you at the time, but it could be the best way.

[Cyne]

Some people always say bars or clubs are a good place to meet women...I've not had any real success there but I suppose that's something you could try. If you're a church-goer, you could meet women at church. Even if you're not, you might go to meet girls.

 

As far as this server you were talking about...you could try to go to the restaurant sometime when they're not busy and hope she's working. Try to strike up a conversation with her or something, and see where things go from there. Also this might sound lame but you could try to ask a friend of yours to talk to her for you. Try to find out if she's available or not, and if she might be interested in you. It might embarrass you at the time, but it could be the best way.

 

Yeah, I try to avoid the bar/club scene. Where I live, that's all everyone wants to do these days, I have honestly never seen what the big deal was/is with it. I don't drink, so on the rare occasions I do go with friends, everyone just gets wasted and act like idiots anyway, not to mention people try to start fights for no reason and there is always a lot more guys than girls.

 

As for the suggestion regarding the server, I'm slightly more on the shy side of things (probably why I wanted to try a nice letter). It's 'breaking the ice' so to speak that is the most difficult part for me. It would pretty much be impossible to start up a conversation with her while she's working, and I don't want to come out of the blue and start asking her out or something like that... she'd probably be wierded out.

[chitown9]

No no no...no letter. That is something in writing that can be passed around to other co-workers, friends and maybe even a husband. Not a good idea at all!

If I were in your shoes I would try to meet up with her at the restaurant. You will need to do a little detective work to determine what days she works and what shift and which tables she is assigned to. You need to be able to be in the position you were originally when she was serving you...and then just point blank ask her if she is in a commited relationship or not, and if not, can I take you out to dinner and have someone wait on you for a change. Sometimes we just have to take a risk and go for it. If she turns out to be married, has a boyfriend, is living with a boyfriend...anything like that you then have your answer. And it is a very little risk really. If she is in a relationship you just stop going to that restaurant.

 

What do you think of this idea?

[BiCurious2011]

I like chitown's idea...but I realize it can be hard if you're shy. What did you think of my idea to have a friend ask for you? Is that not possible to do?

[Cyne]

Well, I'd say it's way out of my comfort zone, I'm definitely not one to just come right out like that and ask someone out without getting to know the person first before letting myself become completely vulnerable that way. As I said, it's next to impossible to start any kind of conversation with her while she's at work, and I'm not gonna wait around until she gets off work and just out of the blue walk up to her like some psycho stalker, lol. Also, from what I've seen and heard, women don't like random guys walking up to them and asking them out, especially by guys who use cheesy pickup lines.

 

I honestly don't know what I should do, it's a hard call, at least to me it is... bah!

[agatha]

unless you are an awesome writer, a letter at this point would be too much. why not a short note (post-it short, maybe with a small verse) and your phone number?

[Cyne]

unless you are an awesome writer, a letter at this point would be too much. why not a short note (post-it short, maybe with a small verse) and your phone number?

 

That actually sounds like a good idea, but are you saying I should hand it directly to her? If not, what do you suggest?

[Cyne]

Forgot to ask, why exactly would a letter be bad and/or too much? It doesn't have to be long, something short as well as sweet to intrigue her? Spark her interest?

[chitown9]

Cyne, please read my post again why a letter is a bad idea. I think putting anything in writing is dangerous because you don't know her status, for example, is she married? You are working blind and the repercussions from a letter could be tremendous. Do you want her husband looking for you? The suggestion that you have a friend of yours make an inquiry about her is a good idea to rule out any husband or boyfriend. But then what?

 

When I said to ask her straight out and qualifying your statement by saying, " I would like to get to know you better, but I don't want to intrude if you have a commited relationship." That is not a conversation, that is simply a question. If your are not comfortable with doing that then you are not comfortable in doing that. But I will tell you this. There are men out there who will take that chance and they are the ones that get the girl. I guess it is just a matter of how motivated you are.

[Cyne]

Ah, I apologize I misread your previous post. Makes sense, I don't need her boyfriend / husband up in my business if she has either. If I recall, she's definitely not married. One of the first things I notice when someone catches my interest is her hands, and she had no ring, so the chances are slim that she has a husband. I'll have to give it some thought and think about how I should move forward with her.