Hi, my name is Josh and I’m a guy in his late 30’s in the bay area whose looking for dating coaching, mostly about keeping a conversation going with a non-talkative woman. I met a girl online named Susan who is an accountant, and says she likes to travel to San Diego, likes walking round San Francisco, and likes to dance. When I asked how she got into accounting, she said, “I’m good with numbers.” What does she like about her job? She says, “The people around her.” Like about San Diego? “Lying on the beach.” What do you see when you walk around San Francisco? “Just people watching.” Can you tell me interesting stories of people you’ve seen? “Not really.” What about dancing? “I like Salsa!” This a composite question based on past experiences with several women. I’m interested to see what you suggest to get women talking more on these awkward dates since the women I meet seem to give short answers and the conversation ends up going nowhere.
Josh, I don’t think it’s the questions you’re asking so much as it’s that you’re not following through, i.e. sharing back to keep the conversation going, as well as not taking the topics any deeper. The women probably feel like they’re being interviewed instead of having a conversation with you. When she replies with, “I’m good with numbers,” you need to respond like, “I’m pretty good with numbers too, but never thought of being an accountant, how did you choose your profession? Was it by accident or was it something you always wanted to do?” Then share something about your career and what made you choose it.
Also, there’s no where for her to go with a question about interesting stories of people she’s seen in San Francisco. It’s too vague. I’m very talkative, yet can’t imagine how I would answer that. You have to share personal information yourself to keep the conversation going like: “I see people in our city as being quite similar to each other, so what is it you see when you’re people watching?” Also on the San Diego question, say, “Personally I love San Diego because there’s so much to do at the beach and it’s so much warmer there, especially when I was there last January. How often do you go and what do you do when you’re there?” And on the dance question, tell her you’ve never tried Salsa (or when you did, how it went). Then where does she go dancing? Is it a good workout? Say that maybe you should try it, but you really prefer running or working with weights. Give her information on you that gives her a way to connect with you.
Also, all of the questions don’t have to start out so personal. Most people feel more comfortable talking about other topics first. Bring up something topical, but not terribly controversial, such as “These political signs and ads on TV are driving me nuts. I’ll be glad when these elections are over. I don’t remember them being this bad before, do you?” If you just get a yes or no answer, go on, “When I was watching my favorite TV show, “How to Get Away with Murder,” there seemed to be more ads than there was time for the show. Have you seen that show yet, it’s really intriguing…….What’s your favorite show?” Conversation needs to flow and you need to be prepared to carry it when necessary. In this situation everyone is nervous and interview-type questions make people more uncomfortable. You need to try to put her at ease. Start with something you read online about her where you have similar ideas or interests or something going on at the moment where you are, such as, “I wonder if it’s always this hard to get waited on? Have you been here before? I have, but don’t remember there being a problem. The last time I was here I had a great waitress,” etc.
Again, be prepared to talk about any topic yourself that you question her about. Also be prepared to make small talk in between topics. Tie in stories of your own with every topic, let her get to know you and your personality and try to put her at ease.
Of course, this advice also works to keep a conversation going when women are trying to get men to talk more.
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