A
male
age
41-50,
anonymous
writes:I was in a relationship with a woman for 5 years. After a tumultuous breakup, involving her cheating, time has passed and we are friends and I feel great about life and everything. My problem is this: I have been out of the dating game for so long that I am unsure of whether or not this woman from one of my college classes is interested.As briefly as I can:She is a year younger than me, I'm 27, she is a single mother, and, from what I can tell by her statement"I don't trust most things boys say", she has a trust issue or two.I arrive to the courtyard by class 30 min early every day and she always comes out and sits and engages me in conversation. She laughs when I say witty funny things. She does the playful touch thing and is always smiling when she looks at me. We have hung out outside of class several times and each time the conversation flows and we have a great time.Those seem obvious to me and I interpret them as a positive signal.I get confused as to what to do because of the following negative things I have noticed:Multiple times (3 or 4), while we hang out she will mention in casual conversation how her friends like to date and go out a lot but she doesnt like to. She's mentioned that she doesnt like to date. She will mention this horrible sounding ex-boyfriend and then proceed to mention that they hung out over the weekend because "she needs to get laid". That's cool, doesn't bother me, but why mention it? I asked her the other day if I could take her out one night and she said "i need to tell you right now that I don't like going out much", and then said "but we can get a bottle and go to your place and play instruments" (guitar and such)Anyway, not sure if this girl wants to develop a friendship or more. I feel as though I'm completely oblivious to the situation and it is frustrating. If she was interested in more, wouldn't she try to show that? I know she must be very busy with her 2 children.I would love to get a clue and get back to how I was 6 years ago when I had one. Thanks for any help. Reply to this Question
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male
reader, Danielepew  +, writes (27 October 2010):
 I agree with Birdy, particularly in your taking care to think with the big one.
I may add that this woman said she doesn't date much, yet she said she hung out with someone to get laid, then she refused your asking her out, and then she said she can have a bottle or two. History teaches me not to go for this kind of deal.
A
female
reader, happy24birthday +, writes (27 October 2010):
 She IS interested, but she's not going to show that to you more due to her trust issues. The inability to trust really holds a girl back. Take her up on the offer to play at your house. If that goes well ask her out again and tell her you want to take her OUT to make her feel special.
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A
female
reader, birdynumnums  +, writes (27 October 2010):
 Wow. She has a lot of baggage attached, literally; two kids + sleeps with her exes to 'get laid'. I'm pretty sure she's interested, but I'm not sure that this woman is going to be the cure for a broken heart - she sounds like a bit of an accident waiting to happen - to You. That's just my observation after reading this letter.
As far as your 'skills' being rusty - they're not - you picked up on her wanting to chat you up - but you HAVE to choose with your head (the big one) AND your heart; and she really does have an awful lot of stuff going on in her life.
Before you go there - do you really want to be her rescuer? Speaking of which - if you do take her up on that bottle of wine - bring TWO forms of birth control - condoms and spermicide. Obviously, you can't count on her not to have a child out of wedlock, and she may just see you as a rescuer, and get pregnant in order to seal the deal.
AND obviously - these are all speculative, worst-case-scenarios... and I am a stick-in-the-mud for mentioning them - but casual dating is searching for a mate - a long-term mate, that's the basic drive behind dating. It's best to decide BEFOREHAND your list of what you want to find in a mate and the things that for you would be a deal-breaker, but it's best to throw the cold light of reality on things, especially if you are coming off of a bad breakup. I hope you find your beshert. xxx
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A
male
reader, dirtball +, writes (27 October 2010):
 Instead of going out, she wants to come to your place. That's a good sign. She didn't turn you down, she suggest an alternative, a more private one at that.
Her mentioning her sexual needs could be interpreted either way, but I'd say it's more of a hint. She doesn't like her ex, but she's willing to have sex with him. Not the best character sign in my book, but I wouldn't write her off either. She does sound like she has some trust/ex issues that will probably cause some problems if you do start to date, so decide if you're willing to work through those.
All together I'd say she's interested. Get that bottle of wine and see where things lead!
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