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heartbreaker1284 heartbreaker1284 is offline
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heartbreaker1284 is ready for this weekend adventure.

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Hey all,

So I have a very weird situation and I need some advice on how to handle it (especially from a guys POV). This will be semi-long so bare with me. Three years ago I interned on a political campaign for Congress - I had 3 bosses - all men around my age - and I loved it. Unfortunately, due to work things I only could stay for 2 months. After the campaign was over all my bosses found me on facebook and befriended me to keep in contact. At the time I was in a serious relationship and then got engaged.

Out of the 3 of them, only 1 maintained semi-consistent contact over the years. He even wanted to come to my wedding last year but couldn't. When I separated from my husband in March (now divorced) I didn't put up a relationship notification because I didn't want an influx of WTH is going on? Fast forward to July, I changed my status to single. A few days later, my former boss emailed me and asked how I was single and if I was ok. We talked a bit and he ended up inviting me down to D.C. where he lives/works for a couple of days.

I thought he was kidding and I declined the invite saying maybe some other time. In September, he contacted me again and said "get on a plane right now and come visit, I'll pay for it." I laughed and said no (believing he was kidding). Then we come to last Sunday - I IM'ed him to say hello and he immediately started teasing me about not coming to visit. Feeling spontaneous and intrigued I said, "Okay, I'm coming down on Friday." He didn't believe me at first but then he said he would pay if I did. I am a short 1.5 flight away so it's not too bad.

Here's my problem - I am going to go flying out Saturday morning and coming back Monday afternoon. He is a hilarious guy and so nice (I had a HUGE crush on him when I worked there but we were both involved with others). I'm staying with him while I'm there because I do not know anyone else in the city and don't feel comfortable staying alone. He has a pretty prominent job and I completely trust him (he's only 2 years older).

How do I approach this? Is he wanting to be friends or something more? Does anyone think this whole thing is weird or random? I'm not uncomfortable at all but I wonder what he's thinking. He doesn't really flirt with me but he's gotten a bit more so since Sunday. I just want to make sure I go into this with some idea of what may be going on. I don't know how much you all can help but anything is appreciated! Thank you in advance.

P.S. - this is not unusual for me - I'm a pretty free-spirited person and if I want to do something I'll do it on a whim. Just wanted to make that clear
Last edited by heartbreaker1284; November 5th, 2009 at 07:24 am.
- November 5th, 2009, 07:21 am
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Gr8Guyn2008 Gr8Guyn2008 is offline
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Gr8Guyn2008 I'm in love and always will be ... All that was there will be there still

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Just shaking my head in disbelief.

What part of he wants in your pants are you not seeing in his invitation?
- November 5th, 2009, 07:29 am
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Mokkesofie Mokkesofie is offline
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While we are waiting for the guys opinions, I want to say good luck to you. He knows you from work so you can be yourself and relax. It sounds really great and you never know what it can lead to.
- November 5th, 2009, 07:31 am
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heartbreaker1284 heartbreaker1284 is offline
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heartbreaker1284 is ready for this weekend adventure.

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Gr8guy - do not mistake me for a fool , I am well aware of what he may want out of this. In fact, I am so paranoid about men I often fear that's all they want from me. However, we have never flirted (not heavily at least) and from the time that I've spent with him and getting to know him over the years - he is not at all like that. He's a laid back, kinda goofy, nervous guy. I think he is nervous about me coming to, at least he appears to be in our convo's. Which is why I wondered what might be going through his head. I certainly hope he doesn't think he's sleeping with me because it's not happening. I know I need to aware and alert for that though. Thank you.

Sofie - I think it's just going to be a fun weekend, I've never been so he's acting as my tour guide. I'm a bit anxious but I'll try to relax!
- November 5th, 2009, 07:49 am
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Mangosteen Mangosteen is offline
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This girl's opinion is he is interested in at least seeing you again... and seeing where things go. I assume that he is no longer with the person he was with before, either... right? The only part of this whole thing that seemed out of my norm is that he is paying for your trip. Do you think he is expecting something based on that? That is the only part that would make me feel uncomfortable. Otherwise, I think it sounds like a lot of fun! You get to see a friend who may be more than a friend who you haven't seen in a long time! Super cool.
- November 5th, 2009, 07:49 am
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heartbreaker1284 heartbreaker1284 is offline
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heartbreaker1284 is ready for this weekend adventure.

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Mango- I was in such a hurry to type I didn't clarify. He offered to pay and even went to book the tickets after finding me flights but that was the part I was apprehensive of, too. So I told him I would pay (it was $100) but he made it clear that next time he would be covering it.

Part of me thinks he wants to sleep with me and the other part says he's in a gray area and trying to figure it out. I'm excited to see him though and we've had a good time when he's come to visit (2 times) so I think it will be okay. I just don't want to go in totally abrasive, assuming he's only trying to get in my pants, if there might be something else there.

- November 5th, 2009, 07:55 am
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6dle899 6dle899 is offline
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Gr8Guyn2008 wrote :
Just shaking my head in disbelief.

What part of he wants in your pants are you not seeing in his invitation?
TOTALLY agree with you on this, John.

heartbreaker1284 wrote :
Hey all,

So I have a very weird situation and I need some advice on how to handle it (especially from a guys POV). This will be semi-long so bare with me.
Err, no thanks.

heartbreaker1284 wrote :





Three years ago I interned on a political campaign for Congress - I had 3 bosses - all men around my age - and I loved it. Unfortunately, due to work things I only could stay for 2 months. After the campaign was over all my bosses found me on facebook and befriended me to keep in contact. At the time I was in a serious relationship and then got engaged.

Out of the 3 of them, only 1 maintained semi-consistent contact over the years. He even wanted to come to my wedding last year but couldn't. When I separated from my husband in March (now divorced) I didn't put up a relationship notification because I didn't want an influx of WTH is going on? Fast forward to July, I changed my status to single. A few days later, my former boss emailed me and asked how I was single and if I was ok. We talked a bit and he ended up inviting me down to D.C. where he lives/works for a couple of days.

I thought he was kidding and I declined the invite saying maybe some other time. In September, he contacted me again and said "get on a plane right now and come visit, I'll pay for it." I laughed and said no (believing he was kidding). Then we come to last Sunday - I IM'ed him to say hello and he immediately started teasing me about not coming to visit. Feeling spontaneous and intrigued I said, "Okay, I'm coming down on Friday." He didn't believe me at first but then he said he would pay if I did. I am a short 1.5 flight away so it's not too bad.

Here's my problem - I am going to go flying out Saturday morning and coming back Monday afternoon. He is a hilarious guy and so nice (I had a HUGE crush on him when I worked there but we were both involved with others). I'm staying with him while I'm there because I do not know anyone else in the city and don't feel comfortable staying alone. He has a pretty prominent job and I completely trust him (he's only 2 years older).

How do I approach this? Is he wanting to be friends or something more? Does anyone think this whole thing is weird or random? I'm not uncomfortable at all but I wonder what he's thinking. .

P.S. - this is not unusual for me - I'm a pretty free-spirited person and if I want to do something I'll do it on a whim. Just wanted to make that clear
t clear

If you accepted his invitation, to stay with him at his house, you should expect to have sex with him...YOU DO understand that, don't you?

You have no reason to play coy around this, having already been married and divorced within the last year or so; and if you are free spirited and do things on a whim, the sex should be no big deal for you as you can't claim to be a blushing virgin or anything.

Right?


Just go and have fun with him, no holds barred.

You know you want to. So does he. He always did
- November 5th, 2009, 07:56 am
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Sassafras54 Sassafras54 is offline
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Can you not drum up someplace else to stay while you're there? A man who invites you for a weekend in his home and offers to pay your way there will probably be surprised when you don't want to have sex with him.

Or, since it's a short trip away, just go for the day?

If you're interested in him, why make things so complicated right away?
- November 5th, 2009, 08:02 am
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6dle899 6dle899 is offline
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Sassafras54 wrote :
Can you not drum up someplace else to stay while you're there? A man who invites you for a weekend in his home and offers to pay your way there will probably be surprised when you don't want to have sex with him.

I would say that in SOME cases he would get very very angry, too --if this de facto "pay for play" scenario did not turn out the way he envisions it would.

You sound like - in effect, ..... you are being an extreme tease.


Kind of scares me in fact, how this could end. Maybe I saw too many bad movies though.


If I were a young woman I would rethink this. But do whatever you want
- November 5th, 2009, 08:11 am
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heartbreaker1284 wrote :
How do I approach this? Is he wanting to be friends or something more? Does anyone think this whole thing is weird or random? I'm not uncomfortable at all but I wonder what he's thinking.
i am not quite as jaded as everyone else here. this could go one of several ways. it could be completely innocent and he wants to see a friend. he may be interested in you romantically and want to see if you are too, or... well, you know...

you know him best. you are the one that has had the communication with him. you know what to expect. we really do not.

keep your eyes open and don't let it go anywhere you don't want it to go.

and i for one would like to know what happens, especially if it all turns out above board and innocent. we need posts around here to help us restore our faith in people.

good luck!
- November 5th, 2009, 08:12 am
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