Dear Lindsey:

Yes, you shared about this man for the first time 12 days ago, on Dec 9: “Something very random and unexpected happened. I had been messaging with a guy for about 2 weeks… So, he asked me to meet him for coffee Tuesday evening and I agreed… So, it went really well, and he asked him to dinner this weekend.  Anita this might be a long-term thing.  He has his stuff together and he is not just someone I decide to hang out with because I am lonely and also insecure in general”.

In the last two days, you shared: “I have continued to see Jason… this guy lives in a really nice house and has a new car… After coffee I met him for dinner, and it went very well.  He said that he likes me/is interested in me… I did ask him a question… ‘What is a negative quality you have and how has that affected relationships?‘…he declined to answer via text…  His response was odd to me, and I was annoyed. The next morning, he wrote saying that because he was poor growing up, he buys things in excess now as an adult.  Also loses interest in those hobbies and wastes money… It’s a possible red flag but is it enough to end things altogether”-

-now that I understand that this Jason is not the other Jason, I see NO red flag whatsoever about him not answering this unexpected question on text. This question would be difficult for a lot of people to answer because it is distressing to address one’s negative qualities. Answering this kind of question by text is not appropriate. It would take face to face. I am impressed that he answered you the next morning. It indicates to me that he really is interested in you and his answer sounds honest to me.

You can ask him questions but remember that he has the right to not answer, and he definitely has the right to take his time before answering. After all, you are not a police detective, and he is not a suspect. Plus, it would have been fair if you answered your own question in regard to yourself before asking him the same question. And do it face to face, one question at a time, exchanging answers.

What is your answer to your own question?

anita