Question: She’s 36 and I am 31 and we work for the same company.  We went out for a couple of dates and both times had a great time. There was a lot of passionate kissing but no sex involved.  I asked her if she’d like to go out for a third date and she said she’ll think about it. To cut the long story short, that was three weeks ago. She flirts with me but won’t talk about going out.  I stopped asking her after three attempts to get her to either say yes or no.  I do not have any expectations but I am beginning to think that she’s leading me on.  I feel so confused and depressed to a point that I am dreading going to work. Should I avoid her altogether? Should I ask her again? Please let me know how I should handle this.

Answer: This is not a place anyone would want to be but there you are, and you have to deal with it. Three weeks may not be such a long time to wait for an answer — if she’s worth it. You work together so you should at least know  –from direct experience and from co-worker accounts — if she’s the kind to play guys just for the fun of it.  It’s possible that this is her idea of “playing hard to get”.  She probably thinks the first two dates came “cheap” and is raising the stakes just to see what you’re made of.  The fact that she’s being flirtatious often means she’s trying to keep the interest level alive.

I’d discourage you from avoiding her altogether as it only adds to making your situation more awkward. If you feel so strongly that this is interfering with your ability to function well at work, then directly approach her and talk about how this is affecting the work environment for both of you.  This may be a little tricky because if you come across as “accusing” her of wrong doing, her response might be not be so positive.  So make sure you’re not angry or really nervous when you approach her.

I suggest that you start with asking her if she’s noticed that you feel a little awkward around her. Then explain to her that it’s because you can’t quite figure out where she is at since the last two dates.  Talk a little bit about what was “special” about the two dates.  Women are into “emotions”, so don’t just describe the “technical” aspects of the dates (the man way), instead talk about the “emotions” you both experienced.  Be as specific as possible so she knows you “remember everything”.  Throw in a casual friendly “It’s not quite like me to be like this, but here I am.”  That says to her she’s different from all the others and therefore special. Then tell her that you’re hoping that when she’s had time to think about it and made a decision, she’ll let you know.  Leave it at that.

The ball is in her court. If her flirting isn’t just “game playing”, she’ll know how you really feel and that if her intention is to keep the level of interest up, she’ll have to do more than “flirting”.  Go on with your life and don’t act like your life depends on what she says or does.  Puppy-like-love makes you less attractive — and can be a turn off for most women (and men).  Even a woman who finds you attractive in so many ways can be turned off by a man who doesn’t seem to have a backbone or life of his own.  So find things to do that take your mind off thinking about what she is doing or thinking.  When you have other interesting things going on in your life, it never feels like “waiting” at all.

If she does not come to you, she was just leading you on for the fun of it– you’re better off without her.  If she comes to you, go out and have a great time.  Most importantly remember to create some very special “emotions” that you can later “remember”…

Whatever direction this goes, wake up every morning, try to look as good as you can, have a positive outlook and go in there — like a man.  You need your job.  A man with a job is attractive… to most women anyways…

I also highly recommend reading my article: Is He Or She Playing Hard To Get Or Just Not Interested?