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Advice when trying to date someone who is already a friend, whose feelings about me are unknown!?

This is a re-posting since I posted it during the night, hopefully more people will give advice at this time of day! Thanks. Ok so my female friend and I have travelled to work since Summer and have been chatting everyday about how we've been getting on at work etc - really helping each other out. She is a single parent of quite young children whom I have gotten to know also. She has been single for 2 years. In these Christmas few weeks off, I have realised I miss this girl and that I really feel a lot for her. I took her and the kids Christmas presents, and they were pretty underwelmed but then, they are that type of people. At New Year I offered to take her a glass of wine early evening as she was stuck at home and I was busy later. She said they be at relatives and not back till my relatives were arriving so I wouldnt be able to go. I am not sure if this was her just not wanting me there or not. I cant be sure that if I tell her how I feel - how she will take it. Maybe she is avoiding me since I took the Christmas presents round, maybe it was too much? (but it wasnt much at all...) She never really texts me when it isnt about work unless I text her first. Also it is very hard to tell the meaning behind text messages anyway. I am kinda scared to even ask when she is next free. She never asks me over (although it's only been a few times) - I tend to ask if it's ok to go over. I would like to see her one evening when the kids are asleep. She really struggles to get babysitters unless she has like 6 weeks notice! Her friends and family are really really unhelpful. I dont mind visiting her at her place though, it just makes it difficult to ask her on a proper date. Maybe I am too inconfident to tell her how I feel anyway. Plus I cant ask her in a way that will seem like I would care if she said no to me, because we still have to work together! I want to act cool! These things dont get better in your 30s you know... I appreciate any help you all give.

Public Comments

  1. you could try taking her and her child out for a meal, things are never easy when children are involved. if not ask one of your members of family to look after the child ?
  2. I think she is responding to your lack of confidence in yourself by not reacting to you in ways that you would like her to. Next time you see her give her a little hug and say " I really like the time we spend together & I want to get to know you better". (or similar.) Arrange a time to see her (it don't matter if the kids are there) and don't let her flake out & if she does flake find out why or forget her. it is hard for single mothers with kids I know. Don't buy any presents or take her out until she is your girlfriend. Women really respond to a guy who can lead, think about dancing, who leads who...the man or the woman?
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