So there's this woman...

[jakeus89]

She works, and I believe owns, a small ice cream shop just outside of my neighborhood. I must first say that she is absolutely gorgeous and I simply cannot take my eyes off of her when I'm there (but not in the creepy way that sting sang about in that song by the police haha). I walked into the shop the other day and ordered my usual chocolate shake, which are DELICIOUS there, and I waited as it was being made. So while standing there, the womans employee spills the shake all over the counter. Of course I didn't get angry with her or anything, I felt sympathetic and insured them that it was ok, after both the older woman and her employee apologized incessantly. Anyway, I took this as an opportunity to chat a little and show some of my humor. So I said to this woman "Gosh, you know I'm just so upset, I mean it outta be free now, having gone through this disaster, I'm a busy man. That's it, Im going down the street to the other ice cream joint". This made her laugh almost hysterically for a good minute, as i just slipped in little sarcastic jokes, which she got because I had a huge smile on my face. She even played with her hair a little, which struck me as something a nervous teenage girl would do lol. But, I cannot say for sure whether she understood that I was flirting with her. Also, I don't even know if she is married or single and I neglected to look for a wedding ring (next time). How do I continue to show I am interested, what else can I do?

[cougarlite]

Hi JakeUS
Well, Kudos for thinking so quickly to try to make her laugh (which seemed to work by the way if she was giggling). She probably caught your vibe. I would suggest first to find out if she is in a relationship before pursuing further. And since this incident seems to have broken the ice a little you might want to ask questions about the shop, about her? Does she live in the area?, etc. Just by asking the most innocent questions may reveal if she's in a relationship.....Don't be nervous, trust me I am in a very similar situation with a young man I work with and either way I'm sure she'll be flattered by the your attention.....
Good Luck!
Lori

[bayridgebabe]

I agree with Lori, try to get some small talk in, for example do you live in the neighborhood, do you have any animals, who takes care of them ( if she has any) when you are @ work? I bet you children love it that you own an ice cream shop. Keep it light hearted. PLEASE let us know the outcome & "Good Luck" Jake

[vita]

No offence, but your jokes don't sound *that* funny so if she was laughing that hysterically she must have really liked you - good signs!

Agree with the others, keep it light and friendly and make good eye contact while smiling and build it up gradually, depending on the responses. If you can get something in that's a bit more flirty and flattering (but not cheesey and ungenuine) then that really does up the ante. Nothing like being flattered for real - especially when you're older - and, whether she's single or not, she will hopefully appreciate that.

[sonia]

Vita - it was probably the way he said it! Lots of smiles at her and eye contact with her Jake and good luck

[vita]

Originally Posted by sonia

Vita - it was probably the way he said it! Lots of smiles at her and eye contact with her Jake and good luck

Sure. Sometimes you just have to be there. And some people can be naturally funny. I wish I was. Whatever, making someone laugh a lot is always such a good sign, I think.

[jakeus89]

Thank you guys for the support, always good to get feedback. I am a little bothered by your comment vita, it has made me question whether or not I came off as some dim-witted horny guy looking to pick her up, or as someone who was genuinely funny and interested in her. My humor is sarcastic, but not annoyingly so, at least to me. I don't see myself as the type of person who has unintelligent jokes, because I am very proper in my speech (English fanatic) and I HATE a joke that isn't witty. I know what you mean by that. And Sonia is correct, if you say it by itself, it is rather dry and boring possibly cheesy depending on who's saying it, but I felt confident in myself enough to say it. I think this disconnect is what I struggle with most. I want older women, and this woman in particular, to understand that I'm not a child and that I want to be taken seriously. I won't go into detail, but my life is not what most guys my age have experienced. That's the difference between me and the next guy who walks in and tries his luck.

[wetnwild]

Jake, I TOTALLY get your sarcastic sense of humor, because I have the exact same sarcastic sense of humor. I think she got it, since as you said, she did laugh!! Always a good sign!! I agree with the others on making the small talk too!

[jakeus89]

Thank you! I'm thinking about going to the ice cream shop after work, but I might be a little dirty looking, is that a bad idea? haha I look much better clean.

[vita]

aww, my comment wasn't meant to make you doubt yourself. It was a compliment really. It was saying if she was laughing so heartily you did exactly what you'd hoped to do - connect with her. If she was laughing I think it's highly doubtful that you came across as a "dim-witted horny guy". And what you said really didn't sound horny anyway. Try not to worry so much and enjoy the seduction process. It's fun and it's meant to be fun

And nothing wrong with a bit of honest dirt, go for it if you want to