Should I ask for a second date in this situation?

I took my real estate agent to dinner last night. I wasn't sure if she thought it would be mostly a business type dinner but I hoped for more. I got a nice haircut and dressed well and when she arrived she looked amazing. Her hair was all done up and had cute outfit on. We rarely talked about the home search and she even brought up a lot of semi-personal stuff about her life/upbringing/recent breakup and kept the conversation going non stop. Not in an annoying way, but there wasn't any awkward silence the whole night. Two hours later we had a smoke and parted ways. I didn't go in for a kiss or hug at the end becuase I was still kind of nervous about breaking some imaginary boundary. Anyway, I told her to text me when she got home safe and she did and thanked me for dinner, but we dont really talk a lot unless I need to look at a house. I want to ask her out for a drink again. Do you think I have the green light?


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  • You need to make it clear that the next time it's a DATE, with romantic intentions. You already put yourself in messy territory where you are going out with a person who is working for you in a customer service industry where your business is worth a good amount of money. In other words, she will be semi-obligated to spend time with you in order to make money, but that doesn't *necessarily* mean she WANTS to.

    So, you have to be totally straightforward with your intentions, NOW, and let the chips fall where they may.

  • The second date will prove her intent, girls don't usually mention ex's - especially on a first date, unless they're talking to someone who is just a friend or a guy they have no sexual desire in. I'm not sure how well you know eachother, but it sounded more like a casual dinner with a friend /w light banter + house talk than really a date.

    However, I wasn't on the date, so I can't say. On round 2, up the kino, try to get some physical contact in and make some eye contact/ get her to smile. And if things are going well don't just end the night with no kiss or hug or anything - should of tried to go in for a hug on date 1 since it sorta sounds like it went well, but like I said I can't tell from what you stated on the conversation.

  • I'd give it a shot.

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