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Old 05-11-2009, 11:56 PM   #1  
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Hi Friends!!!

I am an amateur dater. I have not been on one date in my 26 years and find myself stumbling around when I like someone. Either I miss opportunities (and just crazy regret it!!) or have a few memories of weird rejection.

So I just fumble with dating and have no idea what to do.

This brings me to my current situation: I have a good friend. We have been friends for awhile but the whole time I have been interested in him. I flirt as I normally do, which is not too obvious (or aggressive) I guess.

He is incredibly uncomfortable with dating and this makes me back off. The last time he dated someone was high school. I think he's really insecure...?

But recently I've been really sure that I want to make our friendship something more.

I'm not sure if he realizes it. And if he does, his dating insecurities make him really unsure.

So it's like the blind leading the blind. If he's interested (which I get the feeling he might be...?), it's just the two of us entering completely uncharted territory.

Another friend recently said to me while we were out to dinner..."Y'all are cute" about me and the boy I'm writing about. And we went to a dinner the other day and everyone thought we were dating.

So I think this means there is chemistry and it's not just me. (This makes me so nervous!)

WHAT AM I SUPPOSED TO DO?? SAY SOMETHING?? WAIT FOR HIM TO DO SOMETHING??

(I don't think he ever will! And I have this little voice in the back of my head saying he never will say anything because he feels like he could do better or that if *I* say something it'll make the friendship awkward or he'll get really embarrassed.) Will it ruin the friendship? I can be friends with someone if they say they are interested and I'm not.

Is anyone else so awkward in the dating thing? Or have advice to help me?? I have NO idea what I'm doing. But I need to do something or I'll get nowhere. And I'm afraid someone else will come along and get him!!

Sorry for the long post, but I am incredibly inexperienced and a classic overthinker.

BUT ESPECIALLY I NEED TO KNOW WHAT TO DO!!

Last edited by jerzygal; 05-12-2009 at 12:23 AM.
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Old 05-12-2009, 12:55 AM   #2  
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I got a late start in the whole dating thing, too, so I can really sympathize with your position! (And I am also an overthinker!) I've definitely had my share of experiences with equally awkward guys where we both stumbled around and never really got anywhere because of our mutual shyness/insecurities.

Now that I have more dating experience, when I look back on those times, I realize I was silly to not just go for it and risk being the more assertive one! In almost every case I've found out later that the guy was interested, too, and would have loved it if I had said something.

You don't have to suddenly kiss him or anything, but I would maybe start a conversation with him about dating in general and try to make the conversation more specific from there. Have you guys been spending a lot of time just with each other? You could say something about how you've enjoyed doing that and that you THINK HE'S A REALLY GREAT GUY and see what he says to that. Either way you may end up with regrets, whether you make a move or whether you don't, but I've found the most painful regrets for me are not the ones I have because I took a chance, but the ones I have because I didn't. As they say, nothing ventured, nothing gained!
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Old 05-12-2009, 01:06 AM   #3  
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Just play it off really casually, if you are too nervous to come right out and ask him. "Everyone seems to think we're dating, eh? Maybe you and I should hook up."

That way you can feel him out on the issue, and if he isn't receptive to joking around about it, then you know not to pursue it further. If he is, then try being a little more direct.
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Old 05-12-2009, 01:14 AM   #4  
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i was going to say pretty much the same thing smallification said, that you should bring it up but make it so it could be taken seriously or in a joking way, then you've given him an opportunity to ask you out or talk about it and if he wants to reject it then he can without making either of you feel stink. You gotta be sneaky! When i was talking my to-be-boyfriend, i complained about how i never got to go to the movies because i had no one to take me It gave him the opportunity to be sympathetic but not ask me out, or he could offer to take me if he was interested Sneaky
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Old 05-12-2009, 01:48 AM   #5  
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omg, that was exactly the situation between my bf and i before we got together!

here's what i did.

i dressed up and/or made sure i looked nice to get him to notice me [guys are way visual] [also, please be confidentchick and realize there are hot things about you and play them up]
and then we started hanging out a lot and then one night i did the whole "accidentally" leave my jacket in the car omg i'm cold bit and he ended up putting his arm around me, and that was our subtle way of telling eachother we were into each other.

why am i sharing this? because i didnt know jack about guys until someone told ME.

long story short

1. look good [that doesnt mean look like a model or whatever crap is on the mags these days, but rather, recognize your good qualities and bring them out. trust me, no one notices your bad points except for you!]
2. hang out more
3. find some way to subtly and yet obviously give him an opportunity to make a move. guys are like coconuts so you need to gently knock them a little to get them all shook up, but trust me, if he's worth it, he'll get the hints and want to do something. guys like to feel like the aggressors even though the women actually hold all the cards, so its like my big fat greek wedding where they trick the dad into thinking that it was his idea.
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Old 05-12-2009, 09:03 AM   #6  
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Nope. I'm an expert at picking guys up, but I can not make a relationship work to save my life. Hence my constant search for an emotionally detached man who likes to hang out once in awhile and doesn't mind sharing. Unfortunately he does not exist.

About your guy -- First and foremost, my gaydar twinged a little. Are you sure that he... likes *likes* women? That is a little odd for a grown man not to have dated since high school, especially if he's not particularly absorbed in a runaround job or something.

I only ask this out of concern for your well-being. You need to be sure that as well as loving and being in love with you, he'll be attracted to you. The first love of my life ended up being gay, and I had ignored the telltale signs during our long friendship before we dated. He pursued me trying to force himself to be something he wasn't. It broke my heart to have to let him go (I figured it out before he was ready to end things and accept himself) and he hated me for it. It was hard to be around him for years, but once the light clicked on and he stopped denying what he was he came back to me and we're like peanut butter and jelly to this day. I just would hate for you to go through that sort of drama and possibly lose a great friend.

However, if you are absolutely SURE that he's hetero then you need to step up your game a little. Dress up. Always smell sweet. BE the hot girl. Flirt with varying degrees of intensity (keep it casual and friendly in public, put on the charm a little more and the come-hither eyes in private so nobody is in your business) and make sure you touch him. Fingertips on the shoulder, lightly touch his hand, his knee, his hair. You are most definitely not the predatory type, so those are ways you can drive him mad without being overt about it. It's more like friendly guidance. If he's into it, it will only be a few nights laying awake thinking about your fingers in his hair before he asks you out on a date. If he shies away, back off and play it off like it's nothing. No dignity lost.

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Old 05-12-2009, 10:00 AM   #7  
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Jerzygal, you just described my current situation almost to the T. At least you don't live with him I feel for you. I think everyone gave really good advice - the hard part is actually TAKING it.
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Old 05-12-2009, 10:15 AM   #8  
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Quote:
Originally Posted by stellarosa27 View Post
Jerzygal, you just described my current situation almost to the T. At least you don't live with him I feel for you. I think everyone gave really good advice - the hard part is actually TAKING it.
What the heck Stella? You LIVE WITH HIM. Let the towel slip after your shower. Done deal.

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Old 05-12-2009, 11:02 AM   #9  
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lol I have my own bathroom in my bedroom and he's already seen me half naked.

In the pretext of not hijacking Jerzgal's thread (got to look out for my fellow NJians) I will save that whole fiasco and our long drawn out history for another time.
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Old 05-12-2009, 11:15 AM   #10  
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This can be mad dangerous territory. The thing is, if you give him an in physically, he may take you up on it, regardless of how he feels about you. Guys, even great guy friends, are kind of notorious for seeing an opportunity and taking it regardless of whether they're actually interested in a relationship or not. Then, you kiss, you can't stop thinking about it, and it turns out he hasn't thought twice.

I think you should definitely figure out a way to figure it out verbally instead of using physical techniques to see if something happens. And be careful!
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Old 05-12-2009, 01:18 PM   #11  
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Originally Posted by NishKitten View Post
About your guy -- First and foremost, my gaydar twinged a little. Are you sure that he... likes *likes* women? That is a little odd for a grown man not to have dated since high school, especially if he's not particularly absorbed in a runaround job or something.
OKay...I was wondering if this would pick up the gaydar. I have to say there aren't clear signs except for lack of dating. But then I also haven't dated and am confidently straight. He claims to be straight but I'm sure people wonder...not sure if ever outright. It's such an awkward conversation.

Is just wondering about that a good enough deal breaker??
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Old 05-12-2009, 01:22 PM   #12  
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lol I have my own bathroom in my bedroom and he's already seen me half naked.

In the pretext of not hijacking Jerzgal's thread (got to look out for my fellow NJians) I will save that whole fiasco and our long drawn out history for another time.
Holla Jersey!!

PLEASE hijack the thread! I'm so intrigued! We can handle both!
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Old 05-12-2009, 01:25 PM   #13  
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Lemme also say this is all REALLY good advice. It makes me nervous!! But all is realistic.

I'll reply more later. I've already spent too much work time on this thread!!
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Old 05-12-2009, 05:39 PM   #14  
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guys are like coconuts so you need to gently knock them a little to get them all shook up
Hahahahaha. LOVE that line! And so true. I don't have much dating experience either (I come from a small town and I was pretty much the only chubby girls in high school, so let's just say the local boys weren't exactly lining up to take me out), but recent experience has taught me that all you really have to do is:

a) Make an effort to look good - even if it's just putting on mascara and some lipgloss. The little things go a LONG way. Men are visual. Find your strengths and play up to them. For instance, if you have nice hair, don't hide it in a bun with a scrunchy :-)

b) Be available Make it a point to let him know you're free and available if he's so inclined. Give him an in. Take Iconised Ghost as an example : she mentioned she didn't have anybody to go to the movies with and gave her man an in to ask her out. You can easily do the same thing. Just mention in passing that you've always wanted to try that little bistro on the pier or see that new exhibit at the museum or go white-water rafting, whatever! (Note : keep your ears open. Maybe he's dropping hints like that too and is expecting YOU to pick up on it *wink*)


c) Get closer Take NishKitten's advice, but tone it down a bit if you're shyer than she is (which I think you might be. ****, even I am not that proactive with guys. I wish I could be as confident as she is!) Try to add subtle touches on the shoulder or the arm when you're talking to him. If you're too shy for that, at least try to get closer. If you usually stand two feet apart, reduce that to a foot and a half. If you're sitting on a three-person sofa, sit right next to him instead of at the other end (or worse, on a separate couch altogether!) It'll give you the chance to get used to being close to him physically and give you the confidence to THEN move on to the fingertips-on-his-bare-arm-or-hair move.

Please keep us posted!!! I'm sending you loads of good vibes. Oh, and my gaydar didn't go off at all, if that helps at al. I have a ton of gay friends and also know a few guys who are just really shy when it comes to dating and, by what you posted, I'm guessing your boy falls in the second category....

Oh, and STELLAROSA, I'm dying to know your story. You LIVE with him?
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Old 05-12-2009, 07:14 PM   #15  
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Haha, okay. Well, firstly, I know I'm chicken and that I have an issue with follow through BUT SO DOES HE.

We met my last year in college, through friends, and I've become part of the "group" - these are the guys I live with. I always had a bit of a crush on him, and we have really great chemistry (or so EVERYONE says).
We did hook up once, he was ridiculously trashed and it might have turned out differently if the cops didn't bang down the door to arrest him as we were hooking up. They were campus police - it was a festival weekend and they were being jerks. We've never talked about what happened, I know he remembers because he told one of my other roommates about it. I don't know what he said about it, Jimmy (other roommate) is very closed lipped about it.

We constantly flirt with each other, and do the whole touching thing, etc. Our problem is neither of us will act. Now, he's a really sweet guy, and I don't know if he likes me or if I'm just a great friend. Honestly, *I* think he just sees me as a friend, but everyone else thinks otherwise. Why don't I talk to him? I have no balls. On my birthday one of my lovely girl friends decided to tell him he needed to give me a birthday kiss, and he was okay with that, and then I almost got arrested (the whole traffic court thing a few weeks ago). So its like every time something almost happens, the cops get involved.

He doesn't have any experience with dating, as far as I can tell, and I have absolutely no self confidence when it comes to guys liking me, etc. Its especially weight related when it comes to him b/c one of his friends once said that maybe he wasn't dating me b/c I was a bigger girl. I don't really believe that he thinks like that, but once that seed is planted.

Anyways - I haven't really been pursuing it - we live together, we flirt, he gives me lots of hugs (or I take them) but I make sure that I'm presentable around him most of the time (when I get back from the gym doesn't count). We spend a lot of time together, he was gone this weekend and I was bored out of my mind, and he was emailing me the entire time he was gone.

If I go according to "he's just not that into you" he's just not that into me, but he's an odd duck. My friend Jessie wants to get more time alone with him (and alcohol) to trick it out of him, but eh. I dunno. He was a big support to me after my mom died, like huge, so I also question whether he's just attentive b/c he's making sure I'm okay, or if he likes me.

For a visual (if any of you watch the Big Bang Theory) think Penny and Leonard. Except I'm not a waitress or blond. My sister says that show is my life. Kinda. But my roommates are physicists - we're mostly biologists and we are so not that smart.


Blech.

Jerzygal - where are you from in NJ?

Last edited by stellarosa27; 05-12-2009 at 07:19 PM.
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