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I have a friend of opposite sex. We see and talk with each other about once a week.

Every few weeks I initiate an unsolicited conversation online (private message on social media).

This person never ignores my messages (and never ignores anyone else either).

How can I ask what they think of my unsolicited online conversations and have them answer truthfully? (i.e., how to ask them if it is bothersome and should I stop?)

Age: 20 to 35 years

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    can you explain why you think it might be bothersome? And why you think if you just ask, you won't get the truth? Are you getting mixed messages from this friend. – Kate Gregory Sep 23 '18 at 1:01
  • @KateGregory Almost all the time I initiate conversation on-line. If I just ask, I think he/she will just say no problem since he/she is the "nice" type and don't want to hurt my feelings. In person, usually my friend initiates conversation. – nprcbulbc Sep 23 '18 at 5:51
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If they are responding to you properly and having genuine conversations with you then there is your answer.

When it comes to messaging, it is stupidly simple to ignore someone, be that bothering you or simple that you do not have time for. If this person is responding, you are not bothering.

That being said, there probably is something to be said for the fact that this person (Based on how you asked the question) doesn't seem to initiate conversation with you. This implies either they are simply bad at initiating conversation, or you are not that important to them.

Regardless of my educated guesses on the other parties thought process, if you enjoy doing it and they are talking back to you then keep doing it. Don't be pre-concerned that you are a bother. If you are, you will get much stronger signals than you currently have.

  • This is a great answer. Imagine asking someone IRL "hey, am I annoying you" while talking with him/her ? It would just look unsecure/weird. Online is not that much different. If you really want to have a feedback, you can, at least, said something like "I enjoy talking with you" and if the person answer "me too" then you're done and you won't look unsecure, just a little bit too concerned even if it can be interpreted as a validation request by some. Looking for validation is really bad and may cause you to "lose points". – Meow Sep 27 '18 at 14:11
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While you can try to decipher his/her behaviour in order to see if he/she finds it annoying or not, you will never know unless you flat out ask "Hey, I've noticed that I am always initiating conversations with you -- how come you don't contact me too? Sorry, it just crossed my mind and I got curious. :D".

Some people are also just bad at initiating contact and may very well enjoy conversating with you, but it has become a thing that you move first. It's very individualistic.

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