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How long would you wait for this woman in this situation?

Tagged as: Dating<< Previous question   Next question >>
Question - (28 November 2011) 2 Answers - (Newest, 29 November 2011)
A female United Kingdom age 51-59, anonymous writes:

A question mainly for guys I guess - if you were in your late forties and rarely met a woman that you were attracted to and then met one that you got to know over several years and really, really liked her but circumstances were preventing you from being with her - ie. if you were her boss, for example but only for another 9 months or so, and your own boss was a female dragon likely to fire you if you started something up, or if you had not quite finished your divorce, or if she had recently gone through a very long and hard ending of a relationship and you were not quite sure how she felt about you - how long would you wait for the woman? I mean, if you thought that she was perfect but you pretty much felt that your own life was a bit of a mess/were doubting whether she liked you the same in return? Would you just wait until she showed you a firm sign that she wanted you? Would it help you to know exactly where she stood in things and how much she liked you, or would you see that as a pressure if your own situation wasn't quite clear enough to begin seeing her in a relationship way?

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A male reader, Xearo Trinidad and Tobago +, writes (29 November 2011):

If I were in my 40's I would have confessed already to her by now, and gotten to know her = form a strong relationship with her and eventually make our lives together.

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A male reader, Daniel the love doctor United States +, writes (29 November 2011):

Daniel the love doctor agony auntWell first let me say that office policies are different for many companies when it comes to relationships at work. But I feel that if the two people are grown, they can see whomever they want. HOWEVER... I usually advise against them, being that office romances has more cons than pro's- and can end up bad and awkward for the two that have dated (even the people around them at work)- therefore causing problems for the company... especially if performance is down.

With that being said, if I really wanted to hook up with her, I more than likely would wait until the 9 months is up( even though a lot can happen within that time like I meet someone else I like, she meets someone she likes,the interest fades, etc)- but I would definitely let her know my interest in her upfront... that is of course after I get a feel for her interest during that time. And if I noticed positive signs that she's interested (or she just plainly told me) and she understands that we shouldn't have an office romance, I would patiently wait for the right time to date her.

If I'm going through a divorce, whether I'm finalizing it, or I haven't recovered from the breakup, I would wait until I'm ready before I attempt to talk to her (or anyone else for that matter) on something more than a friendship level.

If she has just gotten out of a bad relationship, I would understand if she needs her space (as that can halt any thoughts of dating as well), but I would definitely express my interest in her. And if I feel that she's worth the wait...I would wait. How long? That depends. But I would definitely let her know how I feel. In this situation it's always best to have good communication to see where each individual stand during this waiting period. Things can change. So I would continue to maintain (and encourage) an open line of communication with her.

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