Its been a ride, need help with next step.

GoinDeep07

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It's been years since I been on here but I need some help again, thanks in advance. I am 44 years old and have been in a relationship for 8 years and the last 12 months decided it was not working out.

Anyhow last March (09) my GF and I were broke up and I am out at a bar after golfing with freinds. I am waiting for a beer when this gorgeous woman taps on my shoulder, introduces herself, hands me a business card and asks if I would like to meet for lunch sometime. Then I realized she used to wait on me at a restuarant a couple years ago. She (Jen) is now an event manager for a Major hotel she is 26 years old. I said sounds good I will be in touch. We meet for happy hour a couple weeks later it goes awesome, we really hit it off. She gives me her cell phone number. I send her a couple text and get no response over the next few weeks. I give up. What I didn't know then is I didn't have the correct number. I eventually get back with my ex but run into Jen on occassion throughout the summer and she is very freindly. I end up working with her to set up group rates with her hotel and my company. We have a very professinal relationship, also become freinds on Facebook.

This October (09) I happened to look at her contact info on my blackberry that I used to for texting her over the summer and noticed I had the wrong number. I send her an email simply saying "You crossed my mind how are things?" She responded entusistically said we need to get together for Happy hour again soon. I call her a week later, we meet for lunch, I tell her up fron that I am in a relationship but mentioned that I tried to get a hold of her over the summer and we laughed and she said next lunch is on her. The problem is I am still in a Relationship! She hints about doing things together but I never follow thru.

This Dec (09) I see her in a bar, she comes and talks to me, I dont trust myself so I tell her I am heading to another bar to meet freinds maybe I will see her later. Then I send her a work email and mention I will be in California for a small vacation. She sends me a freindly email when I get back "Happy hour anytime on me" then at the end of the email it says she is "going to this exclusive party in Vegas in January" and she "had to rubb it in a little because you get me jealus with all my trips, haha". I see on Facebook she is going with some guy. A few days later she drops a Holiday basket off at my office, we have nice conversation. I mention I have a meeting with Govermant officials next tuesday for an open forum. While at the meeting Jen walks in just before it starts and looks increadible, Although it is open to the public I have no idea what she is doing there. After the meeting I say hello, she politely says hello and keeps walking.

Dec final week, I finally made the decision to end my relationship. I also make the decision to meet Jen and see what is going on, is she interested in me, or did she just want me to be her client. I buy a nice bottle of wine, bring it to her work, we go sit by the fireplace. I am nervous as all hell I tell her I think she is gorgeous and there have been many times over the last few months I wanted to spend time with her but I couldn't because I am in a relationship. I ask her straight up if she is interested in me. She says "Yes" I ask her about the age difference she says "I am good with it..no worries". She asks about my relationship, I tell her I ended it. She said she is "seeing someone now" I tell her that probably best, I should just do my own thing anyhow, she quickly responds that "we could do dinner and talk about it." She also mentions that I am very nervous.

I send her an email a week later just saying I had alot on my plate and thats why I was so nervous and joked about it. She responded and said we need to get together soon. I moved in a new place so I mentioned she could come over for some wine and not to worry if she is seeing someone, we could just visit.....no pressure.

Where do I go from here? She is heading to LV with this other guy in 2 weeks, do I just let things go until after her trip? Do I continue to email her?

A little about myself, I am a succesfull manager in the community I employee about 140 employees. I am fortunate to get compensated well for the area. I am also serious about working out and eating right. I have had other women hit on me in their 20's but there is something about Jen that I can't shake.
 

princelydeeds

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You were playing very hard to get, you showed lots of social proof, you were tight on your game, even though you weren't trying to be. DO NOT MESS THIS UP, BY BEING TOO INTERESTED IN HER! Taking the wine to her job, IMHO was a step in the WRONG direction. If playing hard to get was working, don't screw up, by all of a sudden being very available. If she said, "happy hour on her'" wait until the day before, shoot her a simple text that says, "happy hour tomorrow at 5p?" I wouldn't even tell her that I am no longer in a relationship. I would keep doing what you were already doing and do not stop spinning your plates. She is young and I am guessing that your relationship with her will be fleeting. You sound like you are building her a pedestal, the likelihood of a 26 yr old being "the one" are somewhere between slim and none. Have fun with this chick but do not invest too much into her.
 

zekko

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I agree with what princelydeeds said, with a few additions:
This girl seems kind of aggressive. To me that suggests she might be open to being sexual with you. If this is the case you can blow it by being too timid and hesitant. Kino her, don't be afraid to move things forward physically.
Be light, playful, and flirtateous when you are with her but if you act too interested in her by contacting her too much you will come across as needy and without options. Which is not attractive.
 

Slickster

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Good work!

Do not talk about exes with her ever!

If she already has the trip planned to Vegas with other guy it's pretty tough to get in there now. Even if you did and she still goes on the trip that will probably mess with your head pretty good.

You were doing great with out even trying so you already know what you have to do. Her perception of you is probably that you are well to do and desired by many women. Don't disappoint her. Keep up that image and get yourself out there so you don't actually get oneitis over this one. Stay busy.

She's a young professional trying hard to get with an older man. There's a good chance that she might be a bit of a gold digger. Keep things light and sexual.

Keep us updated

Good luck.
 

GoinDeep07

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Great advice here guys! I could blow her off until after the trip to Vegas or what do you think of this: I shoot her an email stating I am having some pizza and beer/wine at the house and I think she needs to stop by after work. and see what happens. I am staying at a pretty impressive home in the area, she is aware of it and she mentioned in her last email I should think about putting a little get together on. I just dont want her to remember me as that nervous guy from our last meeting. I want her to see the cool confident side again.

I agree she seems a little agressive but she is not sluty very high class acting. One of my employees grew up with her and has nothing but good things to say about her and how hot she always was/is. I too am concerned about the goldigger issues.

In my mind I am putting her on a pedastool. I need to get past it. The only way I know how is to concentrate on another women. Any advice?
 

Tell her a little about yourself, but not too much. Maintain some mystery. Give her something to think about and wonder about when she's at home.

Quote taken from The SoSuave Guide to Women and Dating, which you can read for FREE.

GoinDeep07

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Alright here is my plan. I am going to send her an email Wednesday to meet me at the Resurant at the resort I am staying at. Simply send an email saying "Hey Gorgeous, Diner tomorrow at 7:30 at XXX see you there!" My place is walking distance from the restuarant, I will invite her over after dinner for a tour and a drink. Is this a chump move?
 

princelydeeds

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GoinDeep07 said:
Alright here is my plan. I am going to send her an email Wednesday to meet me at the Resurant at the resort I am staying at. Simply send an email saying "Hey Gorgeous, Diner tomorrow at 7:30 at XXX see you there!" My place is walking distance from the restuarant, I will invite her over after dinner for a tour and a drink. Is this a chump move?
I would slow down the compliments. I wouldn't invite her to dinner, I would invite her for drinks. I would email/text her something very simple like, "AWESOME week at work, drinks tomorrow at 730p?" When she follows withe the yes/no then I would say when/where.

Good luck! Do what you were already doing to attract her. Try very hard not to change a thing.
 

Slickster

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Good advice ^^^^^^^^^^ up there. No compliments. Make her really work for that kind of thing.

The only thing I would add is that when she agrees to your invitation for drinks email her back with a "Good, I know a great place! I'll pick you up at ______"

That way you are taking the lead and giving her some mystery as she doesn't know where you are taking her.

It is a good idea to pick her up that way she has less options as to when she can leave. This works to your advantage whether things go good or bad.
 

GoinDeep07

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I am struggling here a. Last night I seen her photos of New Years on Facebook. She looked gorgeous, Had photos of her out with the boyfreind and freinds and having drinks at his place. I got jealous, got drunk last night, feeling down! Not sure I should even contact her anymore? Any suggestions?
 

Slickster

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Yes, don't be snoopy. I can tell you are on a slippery slope. You are already getting WAY too into this chick. The reason she was interested in the first place is because you were unavailable and cool.

Now you are getting nervous, jealous, and obsessive.

Chill out and quit thinking about this chick like she's something special.

You should be focusing on meeting lots of women. It keeps your head on straight and gives her a challenge.

It sounds like you could have your pick so get on it.
 

Kailex

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I agree with all of the above.

Once you ended your relationship, you seem to have done a 180 and are now making her the focus of your attention, which is in turn, exactly NOT what was drawing her to you.

Read the first half of your OP and then do THAT again.

No more taking wine over, no more compliments, just be THAT guy at the first half.

And stop looking at her Facebook.
 

GoinDeep07

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Yeah, I messed up time to move on! Had to coordinate with her for work today via email for some reservations. I said "looks like your enjoying the holidays and having fun with the new boyfreind. I am happy for you."

Time to move on man, live and learn!
 

FreD_BeaR

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GoinDeep07 said:
Yeah, I messed up time to move on! Had to coordinate with her for work today via email for some reservations. I said "looks like your enjoying the holidays and having fun with the new boyfreind. I am happy for you."

Time to move on man, live and learn!
I probably wouldnt have mentioned anything about her boyfriend, especially if she only said she was 'seeing' someone. Because that dosn't necessarily mean she is tied down. Whos to say she isn't still open to checking out other options. She could've been 'seeing' someone all along but never told you.

Don't assume the worst or let your mind wander, I do it WAY too much, and it is not healthy. It makes unable to do anything but think about her, which makes you want her more and puts her on a higher pedestal. Then you start acting more AFC. Ive got the same problem, and im beginning to realize the only cure is to stop contacting her as much, or at all and seeing how she reacts, then you can lay your cards out and choose your next move.
 

Slickster

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This is a textbook case of what not to do. It shows exactly what happens when you don't give a sh!t. Then exactly what happens when you try too hard, put her on a pedestal, oneitis, etc.

Goindeep you already have been given all the advice you need. Ask yourself "why" you didn't follow any of it?
 

GoinDeep07

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Been doing some soul searching here. Really have been concentrating on myself. Been out the last couple nights, met some freinds at a bar mingled. Getting plenty of attention from the ladies. One texted me late last night and asked to come over. I was so cool and confident for a change it was awesome! she just left. Life is coming around!

I have a meeting at Jens hotel this week. If I happen to run into her cool, if not...no problem. I am going to forget about contacting her again for quite some time.

Slickster....Your right, I got to get my head in the game! I reget the email but I don't think this was the nail in the coffin.
 
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