Recently, I went to a clothing store and there was a hot female employee. She gave me a smile that I thought was an IOI. I tried some lines about her helping me pick out some stuff but that didn't work out too well. It felt very forced. Then yesterday, I was at a restaurant with a buddy and there was a very hot waitress. She must have been around 20 years old or so. She came when it was time to order and got pretty close to me. We got her recommendations on some food and then we ordered some cake and she said that she wish she could have some. The restaurant was pretty empty at this point, so jokingly I offered for her to join us, she said no and walked off. My friend thought I was trying too hard the whole night. Our convo felt forced. So my question for you guys is how do you initiate good convos with hired guns? I always see a lot of HBs at clothing stores and restaurants but I never quite know what to talk about to make it more personal rather than professional. What are some good convo topics and how do you make it seem like you're not trying too hard?

If your alone and are walking around just use and opener and then ask for her opinion. Then ask things like if she likes working there or how long she has worked there. And if you see enough IOIs throughout the conversation say something like next week I will come save you from your job. This could mean either me take her out on lunch break or hang out with her after work. If she laughs or says yea sure then say ok I will give you a call, then say whats your phone number. Make sure not to ask for the phone number but demand it this way she is more likely to give it to you and you dont seem needy.

Firstly, IOI's are different from hired guns.
In a clothes store, they are supposed to be friendly and easy-going.

As for waitresses, I always start by doing something like this, when she asks you for your drink order, say ,"hmmm, im not sure what im in the mood for, ....ok, wait, how about you bring me any drink that you think reminds you of me, blah blah blah."

Then your already standing out in their minds, b/c they are thinking about you and wht to get u, and then when she brings it, ask her why she picked that. Then just go from there.

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--Brad

I generally get very flustered in these situations so thanks for the advice.