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I met guy at a bar - what next??? Please read it through!! Pls advise!!


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So I’m 33 & happen to move the Chicago city very recently from NYC. The first weekend; Saturday I was bored & didn’t feel like sitting at home on a Sat night so I walked myself to a bar having a drink by myself. I ended up meeting two amazing men who happen to start taking to me since I was there alone by myself. They both seem to be very well sophisticated, composed, matured & trust me very friendly & also bought me drinks. Never for a moment did I feel awkward nor uncomfortable talking to both of them. Apparently, to me it looked like both of them were equally interested in me but I have to say I liked the Italian tall man out of two. I get attracted to tall men, this is my mental instinct. He was tall, composed, sophisticated, professional & really seem to care so much for me. Were they both hitting on me? – Yes or No. Apparently, they both did their best to grab attention & treat me as a young lady. We were at the bar for few hours & spoke about a lot wide variety of things starting from politics, professional achievements, career, sports, Olympics & a lot. Clock was ticking in & it was time for the bar to close.


I said I was leaving & they both asked me my number right away. I gave them my number because I did not feel threatened like if they were going to stalk me or so.Then I said Goodnight, I’m walking home. The tall Italian guy I liked ( I don’t want to mention his name) immediately said oh no we cant let you walk this late in the night so we will walk you home . I felt so special. Guys walking girls home is a common thing yes while dating but for a guy I met at the bar, this shows how much of a gentleman he was. His smile, his composure, I was really flattered & impressed. Both of them walked along to m apart to a high-rise then I thanked them for walking me to my high-rise & I said why don’t you guys come have a wine or water, check out my apartment & leave. ( no ill intent here).

I genuinely invited them, they took my offer & came over to my apartment.


They both were shocked with surprise seeing my place because I have a very high end place with show accents, grandfather clock, antiques, chandelier & high end furnishing.

Perhaps they did not expect I would be living in such a high end urban polished apartment. People who see my place keep telling me it’s very unusual for a single girl to live in such a high end apartment. The tall Italian man kept saying he is surprised & never seen a single girl living in such a posh furnished apartment. He even asked me if I have any disorder since I have such a perfect apartment. I clearly felt both of them felt way far intimidated & felt I was way too perfect. They said they would never invite me to their place since they do not have as perfect furnishing apartment as mine.


I explained them I’m a girl & it’s in my instinct to take care of myself & my apartment with beautiful decoration & love & respect my personal space. This no no disorder & this Is the way I wanted to live my life. I have a high paying executive job & make decent money to be able to afford the lifestyle I chose to. He kept looking at my place, my chandelier, my small globe bar, my antiques asking if I do only wear Chanel dresses & handbags.

Clearly they both felt intimated, they had wine & left my place around 2:00 AM.The tall Italian man ( my crush) mentioned he is in between job changes now; lived in Hollywood for 8 years done some production work & moved back to Chicago & is living on doing trading stocks on a day to day basis.He told me he is 41.


I texted them both the next day thanking them for walking me home in the new city. They both responded back & thanked me for wine & equally said we should hangout again.


It’s been two weeks they have not texted me back. I’m more interested in the tall Italian guy , his smile, his composure, his dignity . He initiated walking me home with no ill intent at all. How do I stay in touch with him? – I seriously do not much care about his other friend but I’m interested in the tall guy. Do you think he was intimidated as soon as he saw my place? Did he think he could be unfit since I have a fancy place & a high end executive job? – I don’t care what he is going through, even if he doesn’t have a job, I’m willing to work it out. I have my own little imperfectness & issues in my life. I ‘m willing to work it out with him. Should I add him on FB? – I don’t want to be creepy – Please advise. Guys like who who respects women with dignity & composure are rare to find. I felt I have not met a guy like him in like few years. Please advise me all possible options


Should I text him again? Add him on Facebook? – please let me know. I’m spending this time composing this email because truly want to pursue him & don’t want to let him go. What are the realisitic expectations for a guy I meet at the bar?

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I've been intimated but that's only mental. People are people we all bring different things to the table. If you like 1 hit them up it can't hurt at least you tried. Might want to be a bit careful inviting 2 men into your home at midnight that you just spent a couple hrs with. Good luck

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Really? Picking up 2 strange guys in a bar and bringing them back to your place is not awkward, but texting to take them up on the 'let's hang out' invite is?


Picking up guys is the wrong term here - It was all in good well intent - we chatted at the bar, spoke for hours together & felt secured enough to bring them to my highrise because I have a doorman & also they were not creepy. I wanted to chat & spend some time with them watching TV since I was bored in new city. That's what we did exactly.But now, how do I take it from here. He lives few blocks away from me & I do want to stay in touch with him.

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Was it a gay bar? It's been two weeks, they both have your number they don't sound that interested.

Both of them walked along to m apart . He kept looking at my place, my chandelier, my small globe bar, my antiques asking if I do only wear Chanel dresses & handbags.

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And another note - you keep saying fancy words. Antique clocks, chandeliers, doorman, high rise - you think very highly of yourself. You may have turned them off because they may have realized your confidence was arrogance or that you're high maintenance. It may not be intimidation. Be mindful of this, too - you're coming off arrogant to me, at least.

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1) You are dangerously over romanticizing the evening and the two men


2) Having strangers you picked up at the bar walk you home and inviting them up to your place is......really naive and could end badly for you. I think you are lucky that it didn't, but in the future, do not ever do that. This is not about manners and aww how nice, this is about the fact that you don't actually know these from Jack. Sure, 99% of the men will be decent, but if you happen to run into that 1%, you might not live to talk about it. Reading that part of your post kind of took my breath away....not in a good way.


3) Yes, if the guy is between jobs and he saw where you live and how, he is likely intimidated. Let's hang out again is a very vague non committal type statement that usually is a dismissal. At any rate, you don't know him, what he is like and tall is a poor qualification for dating. Regardless, if you want to get to know him and see what he is actually like your only option is to put on your big girl panties and ask him out. Maybe he'll respond, maybe not. You kind of sound like you are in a state where you are prone to making some really bad decisions about life and relationships if something like a drink and a chat at the bar sweeps you off your feet like that......

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If this post is real, then girl....kudos to you for having all that posh apartment and fancy job, but....do not do what you did ever again!!! I don't think you realize how lucky you were that the guys turned out to be decent people, you could have ended up a lamp shade, and all the goodies in your apartment stolen.

You can't trust people just because they seem trustworthy in the grand total of 2 hours you must have spent with them. In fact, serial killers were said to have been very charming and normal looking, and yet they did what they did. What you did was irresponsible at the very least, and could have ended extremely badly for you.


On to "you're a girl so you can't message them" - you're a grown a$$ woman, and this is 2016. If you want something, you go for it. At least, you try. Isn't that what being an executive is all about? You of all people should know how it goes.


Lastly, don't expect them to respect you. Look at the facts: you were alone in a bar, chatted up a couple of guys and invited them over, just like that. I think that's what must have creeped them out, if anything. They may have been the ones worried about becoming skin suits! I can promise you it wasn't that they were intimidated, or in awe, and they certainly didn't think you were too perfect lol. I have no clue how come they didn't try to put the moves on you, I can only assume they were either married or otherwise not interested. But there is only one way to find out for sure: pick up the phone and message the guy you liked.

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And another note - you keep saying fancy words. Antique clocks, chandeliers, doorman, high rise - you think very highly of yourself. You may have turned them off because they may have realized your confidence was arrogance or that you're high maintenance. It may not be intimidation. Be mindful of this, too - you're coming off arrogant to me, at least.


I was thinking the same thing with the wording she's using. But not in the sense that she sounds arrogant, but I'm questioning the validity of the post all together.


Something just doesn't seem right, the grammar, wording, etc. It doesn't sound like the way an executive would talk. If I'm off base and you're from another Country, I apologize. Something just seems off base with the whole story to me.

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First of all, welcome to Chicago, I really love it here.

I believe I understand what is going on. You dont want to take the initiative because deep down you want your man to be a man of initiative. Could it be something like this?


This is what I was going to say. Although, I would add a fear of rejection or looking bad. It seems that you simply don't want to put yourself in a compromising position.


This is contortion, trying to get around the fact that you obviously need to do some initiating.


Send him a text. Nothing dramatic - just check the pulse.


Typically, I do this twice over a week or two. Two unanswered texts (maybe just one in this case) means that you will have to move on.

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On the other hand, if she wants a man of initiative that she can respect, this one does not seem to be it. Why waste the time?


Depends on why he isn't initiating.


If he isn't doing that because he's scared, then he's low-value.


If he isn't doing that because he has options/busy life/lack of need, then he's high-value - or pursuit worthy.

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I haven't read it all , but something is off ..I got as far as you saying why would you send the first text when you are the woman ..after you had gone alone to a bar which takes confidence , you drank with two men you have never met and asked them back to your apartment ..alone ...nah


Yep, a few of us cottoned on to that, lol. hmmmmmmmmm ..........

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