During a professional conference I met a woman about 10 years older than me (I'm 27, she's divorced and has a 2 year old kid).

She was fine as hell, conversation was good (50% professional 50% personal) and I sensed she might be interested. Luckily it turned out we work in the same company.

A few days later I sent her a work email (only way I could get a hold of her) and thanked her for her help, and made it very easy for her to continue the conversation in case she was interested. She did, and she even suggested we meet at the workplace.

A few days go by and I meet her at work for coffee (about 30 minutes), the conversation was great (about 90% personal this time), though I didn't try to escalate anywhere (she can get me fired easily ). This time she suggested we meet at her place in the evening (she lives nearby) to continue our professional talk. At this point I thought it's pretty clear she's into it. I took her number.

So I come over to hers a few days later, and to my great disappointment the whole thing was work related. We spent about an hour sitting at her kitchen counter talking work (she helped me with some project) while her kid was right there next to us watching a Pixar movie. I couldn't get personal with her for some reason, the whole thing was strictly professional. Lots of eye contact but zero sexual vibe and zero contact. I felt like she wasn't into it at all. Wtf?

After we said goodbye I texted her. I wasn't expecting anything at this point, but it went something like this:

clayface: "Thanks again for your help. I'd be happy to see you again sometime, regardless of work" (was a long shot, I admit)
MILF: "Sure, you're always invited for more coffee" (no thanks)
clayface: "I was thinking more than just coffee. How's Thursday?" (trying to escalate a little)
MILF: "My kid is with me on Thursday. What did you have in mind?"
clayface: "A boring movie and some cheap wine. I'll get the wine, you try to find a movie that isn't Disney/Pixar" (that's all she seemed to have around the house. At this point it should be perfectly clear that I'm interested, if it wasn't already)
MILF: "I'll try to get a babysitter. If I can't, is Friday good?" (I assume she's interested too)
clayface: "Yeah, Friday's good"

I pinged her again Thursday morning with a nice opener, then the conversation got kind of weird. Apparently I didn't make it clear enough that the whole movie night is supposed to take place at her place (she doesn't leave the house much, her life is pretty much work and her kid):

MILF: "Can't go out today, but you're still invited for coffee. Sorry"
clayface: "Huh? We weren't supposed to go out.."

And that was pretty much that. No response.

I want to see her again, but I don't want another night of talking as friends/colleagues in her kitchen next to her kid. I suspect the whole "invited for coffee" thing is just her being nice or lonely. I really have no idea where this is going and if I can steer it in the right direction.

What do you suggest? It's a shame, I really like her.

ping her in a week and see if her logistics/interest level has changed, otherwise let it go, chances are slim

move on

Sounds like a shit test. The whole thing. Especially beof the kid! Testing you..

... Just no.

It's not a shit test. Listen to detox.

How come?

How come? Do you know what a shit test actually is? It's a girl testing your meddle and seeing what you'll do in the face of a challenge. Will you back off and go beta? Will you ignore her or respond appropriately and keep your frame?

I really think this was a girl who agreed to a date, and the logistics weren't clear so the date didn't occur.

Thanks guys! You were 100% right, I fucked up the logistics, didn't explain myself very well.

I didn't continue the texting after my last message. She ended up texting me the next morning asking what the plans were, and I said I thought about having a movie night at her place. She thought we were going out on a movie date (like I suspected) which is why she wanted to get a sitter, and couldn't. Anyway, we cleared that up. Lesson learned: BE CLEAR WITH THE LOGISTICS!

I was out of town the next night so we didn't meet, but we agreed on rescheduling. Though there's a problem: I want to set the date for this Friday because her kid will be with his father and it'll be easier to work my magic that way, when we got her house to ourselves, no babysitter required.

I usually go for instadates but this one is almost a week away, and I need to find some way to keep the interest alive until then. Any suggestions on this? Thought about pinging her Tuesday or something, though I'm not sure it's enough and frankly I don't have much to say.

Already got a back-up date with a FWB set for Friday, so no worries this time

Not knowing the time of day your coffee date took place I'd say you're in a decent spot. You're already over at her house just might have to wait for her to put her kid to bed.

As far as the shit test and logistics I wouldn't worry too much about its something you can joke about later.

I think you should ping her there are a ton of canned openers on here that will make her laugh and then you can confirm your date.

This women is your boss? Sounds like this could be really interesting in my experience older women between the ages of 30-40 are usually pretty much looking for a quick fling especially if she hasn't been dating I'm sure she'll like the excitement. You said this women's life is her kids and work? You flirting and gaming her should break up the loneliness and monotony.

Good luck

Don't over do it. This is a mature woman who is constantly busy with her child and very probably doesn't have guys over all the time. She's probably very excited about this. You can see how hard it is to schedule something like this in so now that the logistics are worked out, don't have more than one good conversation with her until the date and don't get in to any long texting conversations. Let her mind wander, let her anticipate. Don't ruin it for her.

BTW, have a back up plan for if she gets nervous right before you are supposed to come over. She might contact you with "I'm nervous about tonight, blah blah". A good move might be "it's ok, there's a little coffee shop on blank street, I'll pick you up and we'll grab a cup of coffee instead". Get the coffee, or even take her to an upscale bar and let her drink a few glasses of wine, then suggest that you go back to her place, because you've been dying to see that movie. This way she doesn't feel like you only came over to pound.

It doesn't sound like your gonna have that issue, but if she does put up some resistance right before the date, it's a good option, and has worked for me before.