Clueless about men

Hello everyone! I need some advice about my situation, but I apologize if this is long.

First let me say my screen name is Clueless because when it comes to guys, or even people in general, I just don't understand them. I'm 27, but have only had one bf which only lasted about 3 months. I'm a loner and find being by myself to be rather comforting, plus I have serious case of love shyness. Actually it is more like if-someone-shows-any-interest-in-me-I-run-in-the-other-direction shyness. However, lately this has been changing. For about a little over a year I've been getting sort of lonely, but I taught myself to ignore it. Until, that is, this guy at work started paying attention to me. We had been working together for about a year, when he started to talk to me. He's a pretty friendly and outgoing guy so I didn't think much of it. He would sometimes go out to eat after work with another guy we work with and invited me and another co-worker one day. She didn't go, but I did. That was in the summer and since then the three of us have been getting something to eat after work since, but sometimes just me and him go.

He is a pretty open guy and he has told me a lot of personal things that has happened in his life. About five years ago he was in a pretty serious relationship where he was engaged, but his fiance ended it and she eventually married someone else. It left him pretty devastated and he said that she was the love of his life. He has had a gf since then, but he's been single for at least a year if not more and he says he enjoys it. So I figured he wasn't interested in anything but friendship. That was fine, but I feel like sometimes he acts like he's interested in me. He gave me his number a few weeks ago and we text each other at least a few times a week. However, when he texts me he sometimes calls me babe or teases me how if I stayed over his house I could stay in his bed if I want. He won't say those type of things to me in person. The problem with texts are I don't know if he is joking or not. If he just wants to sleep with me I can't, I like him too much now and feel that I am finally ready for a relationship. I was okay with us just being friends, but I've started to become interested in him. Tomorrow, weather permitting, we are supposed to have diner for the first time. It was my idea, but I don't think it is a date. I don't know. What does anyone else think? There is probably more detail I need to give, if so please ask.

PS: He once told me that every girl he has ever gone out with has always asked him out. What does that mean?!?

You're love shy and inexperienced, and he's had his heart ripped out. Sounds like both of you need to take things really slow. Definitely don't blurt out "I like you" over dinner. If he likes to send flirty text messages, send a few back. If that seems to scare him off then back off, but it he likes it, maybe he'll start flirting with you more openly. That he agreed to have dinner with you is a good sign that he thinks of you as more than a friend. But be careful not to become a "friend with benefits", you've already said that wouldn't work for you.

He said everyone he's gone out with has always asked him out, huh? Guess he doesn't like to make the first move!

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Originally Posted by CluelessMe [Dear Guest/Member you have to reply to see the link.click here to register]

Actually it is more like if-someone-shows-any-interest-in-me-I-run-in-the-other-direction shyness.

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Whoa, that's bad. I'm extremely love shy myself but its only like unless-someone-shows-any-interest-in-me-I-can't-make-the-move shyness.

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Originally Posted by CluelessMe [Dear Guest/Member you have to reply to see the link.click here to register]

If he just wants to sleep with me I can't, I like him too much now and feel that I am finally ready for a relationship.

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I agree. He probably does want to sleep with you but you should wait until you know he wants a relationship too.

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Originally Posted by CluelessMe [Dear Guest/Member you have to reply to see the link.click here to register]

He once told me that every girl he has ever gone out with has always asked him out. What does that mean?!?

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It probably means that he is shy but handsome.

Being interested in him as you are, you should try showing it to him at some point to get anywhere.

"Being interested in him as you are, you should try showing it to him at some point to get anywhere."

That is my biggest problem. I don't even know how to show interest. For me the fact that we go out to eat and I can actually start conversations with him means I'm interested, but I know to a normal person that is probably just seen as being friendly. I've been terribly shy since I was a kid, but I've gotten a lot better, so the fact that I feel so comfortable around is a big deal to me. That is what made me realize that I liked him. I just have to figure out how to show an interest without being too forward, but have him still know that I'm interested. I hate over analyzing everything I say to him, it drives me crazy.

Thanks you both for your replies. They helped a lot. We'll have to see how dinner goes.

Try initiating some calls or texts and being flirty in some of them :)

So we had dinner last night and I didn't get the feeling that it was a date, which was good and bad. It was good because I didn't get the feeling he was just trying to sleep with me, but it was bad because I also didn't get the feeling he was interested in me. I still really like him, but I'm glad he is my friend as opposed to trying to get in my pants, lol. He always did try to find a way to touch me though during dinner, and he does that at work too.

However, about 10 minutes after we left he restaurant I was on my way home and he texted me saying that he just realized we should have gone for coffee afterwards. Then we spent a good part of the night texting, he even convinced me not to go to work that night because of the weather. We started talking about his dog and he sent me a picture of him. I asked him if he uses the dog to pick up girls. He said not really, but when they do come over the dog gets a lot of attention. So taking people's advice to flirt with him more I got bold (for me anyways) and asked him when I could meet the dog. He said whenever I like. I then said I should see him the next time we eat out at this other restaurant that he said we should go to during dinner. But he didn't text me back after that, which made me panic a little. However, it was late so I don't know if I was too forward or if he just went to sleep. I hate how he can be sort of flirty in text, but in person he's not. I don't know how to respond to that. What do you guys think?

You're 27 and have had one relationship which lasted 3 months. Did you have sex?
If you are 27 and have never had sex then you have BIG problems. Do you have problems with your social skills?

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Originally Posted by CluelessMe [Dear Guest/Member you have to reply to see the link.click here to register]

PS: He once told me that every girl he has ever gone out with has always asked him out. What does that mean?!?

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I say this often, and it's true.

It means he's not certain whether or not you're into him. If you want anything to happen with him, you're going to have to make the first move, or spend a lot of time waiting.

Why did your 3-month-long relationship end?

He is very shy too. Texting is like having a few drinks....you are a little braver to say things rather than being in person. You need to give him some obvious signs that you are interested...and if possible speak openly about it......take a step out of your comfort zone.

Ok, I'm trying to be more bold. I've already invited him to see a play with me that my friend is in and we text eachother practically everyday now. The texts are always pretty flirty so I'm not sure how he doesn't know I like him. I'll see him at work tomorrow and we'll probably hang out afterwards. Hopefully I won't be a chicken sh*t.

doppelmakemelol, my last relationship didn't last because we basically became friends. There wasn't any real spark, just teenage stuff.

Listen very carefully please: Life is truly an awesome thing, but can be an uncertain place someone like yourself will find awkward based on your previous experiences which are next to nothing...

To understand people: is to meet God in person: shake his hand, and have beers over the talk of how he created life...IT is NEVER going to happen! (not in this lifetime anyway)
So, you need to learn something very important:

WORDS DO NOT = how people feel, ever. To an easy target like you (given your timidity and lack of experience) Men will tell you whatever appeals to you in order to let your guard down: and sleep with them.
ACTIONS =Intent. While you will never truly know how ANYONE on this Earth truly feels: their actions tell us who they are and what they want. Not words.

In a Candid and anonymous setting (like here for example) people tell you how they are by their (written) words, not their "said" words, big differences, they are.
In texts you are lacking all but one of the 5 senses: sight. You can read but you can't touch nor feel them. -Even if they make you tingle because he knows what you want to hear.

So, if you need more advice feel free to post more just PM me.
A guy can call you babe for a number of reasons: the most obvious of which: he likes you.
A guy flirts with a girl he's interested in, no mystery here.

His comment about being in bed had to do with gauging to see if you react to it:
It you react positive and reciprocate (as sexually uninhibited women do) then he would continue (verbal foreplay)
If you didn't like it and say "EEEEWWWWW, Gross" then he could more than likely say, "j/k" or play it off.
I suspect IF you two hang out: and you don't give him sex he will leave you, stop calling and texting and possibly even call you names (in an attempt to push you to sex)

This is why it's good to know yourself, and KNOW who he is: you have zero idea who this guy is...
Are you willing to give up your virginity due to peer pressue OR for some other reasons which may not be pure?