Dating advice needed - pref from a female perspective

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...although men are welcome to comment too, if they think they have any insights that might come in useful.

The situation is this. There's a woman I've known for quite a few years now. She's the co-ordinator of a music quiz puib group that I've been going to for a while. I've always been attracted to her, but until now I haven't said anything, because she's been going out with another regular member of the team for ten years now, and I was also going out with someone else when we first met. However, last week she told me they'd broken up - making us both single - and judging by the fact that she and her ex didn't talk to each other all evening, I'm guessing it may not have been entirely amicable.

I have no idea whether she'd be open to something more than friendship from me. All I can say is that she bought me a drink last week, she laughs at all my jokes, and has recently confided some quite personal stuff about herself to me (which I'm not at liberty to repeat here, obviously) that's convinced me that we have more in common as people than I'd first guessed, although she isn't on the spectrum and is not a member here.

The thing is, she asked me if I could run an errand for her concerning something not entirely legal which I know from reading other discussions on here is enjoyed by quite a few other WP members besides me. I'm about to do this on Friday, and will be sending her a PM with the details, but I'm wondering ... should I just bite the bullet and ask her in the PM if she'd like to meet up, on-to-one, for a drink?

I'm a little worried that she might think I'm being sleazy or opportunistic, seeing as she only split from her ex last month. There is of course also the possibility that she might say she doesn't want to start dating again so soon after the end of her last relationship.

The alternative is that I could leave it for a little while, or perhaps ask her in private the nest time the quiz team meets again (which willl be in the middle of August). However, I'm concerned that if I do that she might get back with her ex again, or someone else might ask her out. I'm wondering if anyone on WP can give me any insights into how they wiould react if they were female and I wanted to do what I've just described.

I know everyone's different and that there are no hard and fast rules about this sort of thing, but I feel caught on the horns of a dilemma here nonetheless. This dating game is so bloody confusing when you're on the spectrum.

She may see u as a safe rebound option. Take it slow

The above, to get back at her ex. Also, the illegal activity is a big red flag. Does she care for your welfare? Why is she having you take a risk instead of her doing the illegal activity herself? That would actually piss me off.

I'm not sure about the getting back at her ex part, but I would also be concerned about the illegal activities. If she is doing things you don't agree with, I definitely wouldn't put myself at risk, just to make her happy. Remember, it's your butt on the line, not her's.

I would be cautious about this one.

i would ask her out promptly. if she says it's too soon, you can always ask again later. but as others have said, don't give your heart away until you know this isn't just a rebound thing for her. i know when i broke up with my fiance for hitting me, i was very happy to have company right away. and i'd hate to have you miss out to someone else because you waited.

A sticky wicket .... I would get her the weed, but don't ask her out at the same time unless she hints. She could be using you as a link, especially if her ex was her dealer. But this doesn't mean she doesn't like you as well. Take it slow and try to read her behaviour.

She sounds like trouble to me.

OMG.....I am agreeing with angela.

I sense changes in the weather already.

Can I just clarify re. the illegal activity - I'm not specifically going out of my way to do it for her. I'm partial to a smoke myself and I have a contact that I see once a month or so, regardless, so all she asked me to do was buy her a little extra which she'd then pay me for. Also, I don't think her ex-boyfriend was her dealer. I had no idea she was even interested in the stuff until it came up in conversation last week and she asked me - apropos of nothing - if I could get her some.

I do take on board the rest of everyone's points about the possibility of her being on the rebound or doing it to get back at her ex, though, so i am indeed going to take it slow. I'm just going to invite her for an informal drink - without there being any suggestion of it being a date - when we meet to do the transaction, and I'll decide from there whether I think it's worth pursuing further depending on how it goes.

Thanks to everyone for the responses - they've all given me food for thought, even if some of them contradict each other.

Was going to say that it sounded like she was buying you the drink and laughing at your jokes because she had a favor she wanted from you. When you mentioned her wanting you to get her drugs, it sounds (to me) like she was trying to make you like her so that when she asked you for a favor you would be disposed to doing it.

If a woman shows an interest in you and then asks for a favor, always take it with a grain of salt.

I see your point, but it didn't really happen like that. The laughing at my jokes and buying me a drink happened earlier in the evening, and it was only later on that the subject of weed came up - and then only in the context of how much stricter her parents were than mine (because mine let me smoke in their house and don't care, as long as it's only in my room. Not that I still live with them, you understand, but I visit once a month or so). She then asked me, totally off-the-cuff, if i could get her some the next time I saw my contact.

Anyways, we're meeting for a one-to-one drink later in the week, so I'll see how it goes from there, if if goes anywhere at all.