Not sure if the one I like is into me...

So, I am in the my early 30s, male, and fairly good-looking. I have been so occupied with my work over the past 5 years I haven't really had much time for dating. I had decided after spending the holiday season feeling alone that I'd get myself back out there. After a bit of a dry spell, and by sheer coincidence, a couple women re-appeared in my life and suddenly I have to decide if either are worth pursuing. Woman #1 is someone who is a couple years old, recently divorced, and has a couple kids. Apparently, her now ex husband wasn't as nice of a guy as I had thought. I actually knew both of them somewhat over the past 15 years, and I like them both. Out of nowhere, she reached out to me, asked if I was single, then started mentioning there was no longer a man in her house, blah blah. I kind of felt she was in a bad place and was latching onto me. And she started contacting me frequently. I will admit I felt a bit suffocated as while we've been "friends" we have never really been that close, and, I've only really seen her maybe 2 times in the past decade! A couple days ago, I awoke to some texts from her, one of which asked if i was at all attracted to her. After a while I responded that while I likely would've considered something when I was younger, I felt it was best we not get involved because at my current age I've found these types of situations to get really complicated and i didn't really want that to happen. Anyways, she responded back to it didn't have to be complicated, and she could see herself having a friends-with-benefits type situation. I mean, I guess it was somewhat flattering, but, these types of situations never end well in my experience, and, this isn't really what I'm looking for. Plus, it feels wrong, as while he may very well have been a lousy husband - I really liked her husband and feel I'd be doing something wrong if I did sleep with her. Sorry for the rant, but I just needed to get this off my chest as I really have nobody I can tell.

The second girl is someone I've known for a few years as an acquaintance, but she is really good friends with a friend's wife. She brought her friend over to my house, and, I gotta admit, after spending a little time and talking I was actually starting to become interested. She's clearly smart and has a good head on her shoulders, and I found we have some overlapping interests. I do, however, wonder if she's picked up on my attraction and is teasing me a bit. I will give an example. I was sitting next to her on the couch, and our mutual friends were on the loveseat. She asked me if she could have a lighter. I was about to reach to my right, pick it up, then hand it over to her (she was seated to my left). Before I could, she literally got into my lap and crawled ACROSS me to grab it herself. I gotta admit, it was a first. When this happened, I instinctively looked up at our mutual friend in a confused face, and she kind of rolled her eyes at what I am guessing was her friend's antics. So, I know nobody here is a mind reader, but I am not sure if this is a sign of attraction, or, just someone who likes to flirt for attention.

Exactly what kind of woman are you looking for?

Imo, the first girl indeed sounds like a no no. The second girl probably does find you attractive. Her approach sounds over the top, but I doubt that she did it just for attention. If you decide that you like her, ask her out. If she declines then you have your answer, no harm done.

Well you could ask the second woman out for coffee and just spend some time with her and see how it goes? Also you have plenty of other options that are not these women. What about doing online dating? Meetup.com? Hobby groups? Go to more parties?

Avoid number 1. That sounds like a world of pain in waiting.

Number 2 ask her out, mystery solved.

Exactly what kind of woman are you looking for?

A nice girl with a good head on her shoulders. Employed, able to manage money. Someone who likes to travel, laugh, preferably with no kids, but it wouldn't be a showstopper give my age.

That's my plan, honestly. I have already decided #1 isn't a good idea, though I am using it as a slight confidence boost that there's women out there who'd like me.

#2 I do plan on asking out, I just found her crawling my lap to be a first. I mean, maybe there's guys out there who had this kind of stuff happen to them often, i'm just not one of them!

I am thinking meetup to find people locally with similar interests. And, just living life and trying to be a happier person, exploring old and new passions. Bound to meet someone.

I mean, maybe there's guys out there who had this kind of stuff happen to them often, i'm just not one of them!

Yes you are, apparently.

Go with #3, the one you'll meet when you get out more and join some clubs and groups that interest you. The one who volunteers in a place you have an interest in, the one who is in one of the classes or courses you are interested in taking. Or the one who is an a quality (paid) dating site.

The 2 you mention are merely expedient. 1 is a no-go and 2 you already disrespect.. You need to make some effort.

She's clearly smart and has a good head on her shoulders, and I found we have some overlapping interests.