This person presumably has some specific things you’re looking for in a companion. You can ask about the basics but move on to things that genuinely interest you: how they think, what they think about, why they reached out to you, what they are looking for
Illustration/Uday Mohite
I have a profile on a matrimonial site and whenever a girl accepts my chat request, we start by talking about the usual stuff. After a while, those conversations become forced and awkward, and two girls have complained about this before terminating all contact. All my interactions have been ended by the girls so far. How do I keep the conversation flowing, when the girl doesn’t make an effort (or hardly any effort) to keep the momentum so I can take this to the next stage? I realise now that I have been struggling with this my whole life. I didn’t exactly date before and have been luckless in my search for a partner over the last six years. I am running out of hope and running out of time.
— Jonathan S
If you know you have a problem with conversation, there are things you can do to focus on this instead of worrying about interacting with women. Start by speaking to women you aren’t interested in dating and ask your friends what they think you’re doing wrong. Some people prepare notes before any conversation and create a list of topics they think they would like to discuss. Things only start to seem forced when you aren’t paying attention to what you want to talk about. You are looking for someone you want to spend the rest of your life with. This person presumably has some specific things you’re looking for in a companion. You can ask about the basics but move on to things that genuinely interest you: how they think, what they think about, why they reached out to you, what they are looking for. This isn’t easy, but it only gets easier when you speak to more people.
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