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  1. #26
    Still Hates Small Ball Spurminator's Avatar
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    I think she's made it pretty clear that she's interested, and this is coming from a guy who has been about as oblivious to that kind of thing as you can get. IMO, she's been so forward about it that if you don't make a move soon, she is going to feel rejected.

    I think a group happy hour is a good idea, but I disagree with the idea of not sitting by her or starting a conversation, because she may be waiting for you to do that. With the signs she's been throwing out, I'd say the ball is in your court.

  2. #27
    Murdering Prostitutes Findog's Avatar
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    I'd advise the first plan. Plan B looks good on paper but there's too much that can go wrong. Chances are that something would go wrong and you'd be in the same boat you're in now but even more uncomfortable.
    The other thing I thought about was that initially you'd want to keep things discreet, assuming mutual interest. Suppose you end up getting into some deep, involved conversation in front of several of your coworkers. People will notice that.

  3. #28
    Still Hates Small Ball Spurminator's Avatar
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    Also, I don't know where you're at as far as looking for a good time vs. looking for a potential mate, but make sure you guys are on the same page before you do anything serious. The risk you're taking with her as a coworker isn't that great when you're sleeping together... it's the breaking up part that gets messy.

  4. #29
    GTL: Gym, Tan, Laundry Thunder Dan's Avatar
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    she is in your league, have some confidence. Just go at her like you are the catch. I mean when Pam Anderson didn't have kids she was with Tommy Lee, after she had 2 kids, she was with Kid Rock.....

  5. #30
    I am that guy RandomGuy's Avatar
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    A) on a Thursday, ask her what her Friday happy hour plans are. That gives her plenty of time to find a sitter if she's interested, and by leaving it vague and low key, I can play it off as a misunderstanding and one coworker pal trying to hang out with another coworker pal in the unlikely event she throws the sexual harrassment card in my face.

    B) get a group together for a happy hour thing. See to it that she gets an invitation and that she knows I among others will be going. I should not be the one to hand out the invite. If she shows up, don't sit next to her. If she gets up to come talk to me one on one and engages me in this setting, as the theory goes, then that's the confirmation I'll need that she's interested as opposed to just trying to find somebody to pay attention.

    I don't know if either of these plans are good though. I know if I do make an approach, I have to be strong and confident, with kind of an indifferent air as to whether or not she's interested. So far I've played it cool and she's generally been the one initiating conversation.
    There is a fair chance she is interested. Males tend to overestimate a female's interest (it works for us biologically, but makes us do stooopid things on occasion), but in this case it seems a fair bet that she wouldn't invest so much chat time in someone that she wasn't at least halfway interested in.

    If I were you, I would stick to a nice safe plan-A style couple of hours at a fairly quiet, nice restaurant or fairly low-key bar.

    She is a grown up, so it is best to keep it from being too loud.

    One tip drilled into me by my wife of 14 years:
    Women spend a fair amount of effort on their appearance, i.e. shoes, hair, dress, etc, and men will unconsciously note "those shoes look nice" or similar, but often neglect to say anything.

    Find something you genuinely like about her outfit and compliment it. No fake-y sucking up, just a nice genuinely-felt compliment.

    One possibility:

    There is a nice small bbq place near the San Antonio Zoo. I'm not sure it is still there, but you could simply make a date to go to the restaraunt, and if the weather is nice, take a nice walk afterwards. Depending, you could even choose the to see the Zoo. Something like this creates a common experience that can foster a relationship a bit.

    Scout around for something like this, i.e. a nice/medium restaurant near a park or other place to take a walk while the weather is nice.

  6. #31
    I am that guy RandomGuy's Avatar
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    The other thing I thought about was that initially you'd want to keep things discreet, assuming mutual interest. Suppose you end up getting into some deep, involved conversation in front of several of your coworkers. People will notice that.
    Agreed. If it is at all frowned upon, and even if it isn't, then this is probably the best way to go. Gossip sucks.

  7. #32
    Forum Official Personal Life Coach BacktoBasics's Avatar
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    This thread is weird. If a women asks: Did you miss me or are you missing me. She's calling out for attention and wants to feel wanted. She wants sex. Why is this so complicated. If it develops into something more great if it doesn't great. You won't know until you dip your balls in it.

    I would ask her out like a real man. Don't pussy foot around it. Then if the date goes well you might want to bring up the discreet aspect of your jobs to gauge her reaction.

    99% of women are attracted to someone forward and direct. Blunt even. Pussy footing around only works with fatties.

  8. #33
    I am that guy RandomGuy's Avatar
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    Also, I don't know where you're at as far as looking for a good time vs. looking for a potential mate, but make sure you guys are on the same page before you do anything serious. The risk you're taking with her as a coworker isn't that great when you're sleeping together... it's the breaking up part that gets messy.
    Agreed.

    I wouldn't go for this one unless you were at least willing to think about marriage. You can bet your ass SHE will be keeping that in the back of her head.

    Her child complicates her relationships immensely. If you really like her, keep this in mind and any gestures you make that show you understand where she is coming from will be noticed.

    Don't suck up to her kid. The kid will know at some level what you are doing, and that isn't healthy for anybody. Be polite, and remember that her child should NOT be your friend. If you really do end up in a serious relationship, you will have the duties and responsibilities of being a father instantly. Always keep that in the back of your head. Fathers are NOT friends. They are teachers, rule-setters, and guides, with the ultimate goal of producing a capable, polite, competant adult.

    If you really really like her, and you act like a father (don't push it at first though), she will instinctively know that, and it will strengthen the relationship.

  9. #34
    Forum Official Personal Life Coach BacktoBasics's Avatar
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    I think its way to presumptuous to think that a single mother wouldn't want casual sex.

  10. #35
    I am that guy RandomGuy's Avatar
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    This thread is weird. If a women asks: Did you miss me or are you missing me. She's calling out for attention and wants to feel wanted. She wants sex. Why is this so complicated. If it develops into something more great if it doesn't great. You won't know until you dip your balls in it.

    I would ask her out like a real man. Don't pussy foot around it. Then if the date goes well you might want to bring up the discreet aspect of your jobs to gauge her reaction.

    99% of women are attracted to someone forward and direct. Blunt even. Pussy footing around only works with fatties.
    Good points both.

    She could just want to get laid, and it could be as simple as that. Don't assume anything, but keep your eyes open.

    Women dig confidence. Don't be an ass, but don't be afraid to be a *little* bit forward at first.

  11. #36
    Forum Official Personal Life Coach BacktoBasics's Avatar
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    Good points both.

    She could just want to get laid, and it could be as simple as that. Don't assume anything, but keep your eyes open.

    Women dig confidence. Don't be an ass, but don't be afraid to be a *little* bit forward at first.
    At my last job before I met my wife all the women in the office were single moms or on their way to divorce. I slept with 3 out of the 8 available and none of them wanted anything more than a few hours of attention.

    I'm all for being cautious with women because most can't be trusted but lets not forget how overly emotional women are....and with that comes stupidity. She seems to want some attention and it seems that she's trying to do that without coming across as the office .

    Read between the line....or better yet just read whats right in front of you.

  12. #37
    Ina world of hype, we win IronMexican's Avatar
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    Hope all works out for you, bro. I'm going through girl problems myself, and I know how much it sucks.

  13. #38
    right about pizzagate Blake's Avatar
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    I agree that this thread is weird.

    My instinct says that this is a bad idea. I think she pretty clearly sees you as more than just a one night stand.......but if you do just hit and quit on her, you have to see her in the office.

    but then again, you may pull off the Jerry Maguire and be a happy guy with her and junior in the end....

    I still would say no.

  14. #39
    right about pizzagate Blake's Avatar
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    At my last job before I met my wife all the women in the office were single moms or on their way to divorce. I slept with 3 out of the 8 available and none of them wanted anything more than a few hours of attention.
    wow, who knew that staring at women's crotches all day actually works....

  15. #40
    Maaaaaannnn fuck.... E20's Avatar
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    Just make sure she doesn't shoot any unexpected shots. Can't have that happening.

  16. #41
    Murdering Prostitutes Findog's Avatar
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    Just make sure she doesn't shoot any unexpected shots. Can't have that happening.
    She's just making the pass at me that she's supposed to make. No surprises there.

  17. #42
    俺はまんこが大好きなんだよ baseline bum's Avatar
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    You know where to take her on the first date:


  18. #43
    Murdering Prostitutes Findog's Avatar
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    You know where to take her on the first date:

    haha...we actually do business with Yum Brands. There are KFC executives in the building today.

  19. #44
    No darkness Cry Havoc's Avatar
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    Dude, just walk up to her and compliment her, then ask her out.

    Something like, "Listen, I know we've been talking a bit lately"

    and then ask her out. Most women will appreciate the straight-forward approach.

  20. #45
    No darkness Cry Havoc's Avatar
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    AND FOR CRYING OUT LOUD POST A PICTURE OF THIS FINE LADY!!!!!

    If you don't, we'll kill you. Or find out who she is and show her this thread.

  21. #46
    Believe. Milton.'s Avatar
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    I think you should spend more time trying to get some action and less time wondering what the others think. Will it make the experience more pleasurable for you knowing that we are somehow involved simply because we know all the boring details of your pathetic dance around a potential gold mine of uninhibited wild sex? You need to get your priorities straight. That's what I've been told.

  22. #47
    Beware of the Voices Bigzax's Avatar
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    wear a rubber dude.

  23. #48
    Spur-taaaa TDMVPDPOY's Avatar
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    tell her you like anal sex, she will definitely go out with you....

  24. #49
    俺はまんこが大好きなんだよ baseline bum's Avatar
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    tell her you like anal sex, she will definitely go out with you....
    Does that work for you? Do you offer to buy her the strap-on too?

  25. #50
    I am that guy RandomGuy's Avatar
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    Does that work for you? Do you offer to buy her the strap-on too?
    Oh SNAP!!

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