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"enter into a conversation" is a correct and usable phrase in written English.
It means to start or join a conversation. Example: I was hesitant to enter into the conversation, but eventually I found the courage to speak up and share my thoughts.
Exact(14)
"They were happy to enter into a conversation with us, because they're having a recession too".
Wearing jeans and a sweatshirt, she shook hands with two reporters, but would not enter into a conversation.
"There is always a need," he said, "to be able to enter into a conversation and have your contribution judged for its merit and not who you are".
Reds are very reluctant to enter into a conversation with Blues, for fear of further shaming, but they often come to the table when they are told that this will be a chance to "de-monsterize" themselves.
When readers enter into a conversation with any of our titles, for example through the use of polls, comments, text messages, email, phone, radio or letters we reserve the right to display this content indefinitely in any relevant context subject to our editorial judgement.
On Her, users only enter into a conversation when both parties have liked something on that users profile.
Similar(46)
This happened to me about a year ago when I entered into a conversation, via email, with Baz Luhrmann, the director of the glittering new film version of The Great Gatsby.
It felt sometimes as if the overtones of the notes themselves had entered into a conversation with one another.
When DeChristopher enters into a conversation, other activists drift in his direction, just to listen to what he is saying.
That's our first step into disseminating, or entering into a conversation with other schools and school districts about doing lesson study," said Fernandez.
Through his drunken haze, he enters into a conversation with an inanimate object, in this case, the decorative handle on the tap of Shock Top beer.
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Since I tried Ludwig back in 2017, I have been constantly using it in both editing and translation. Ever since, I suggest it to my translators at ProSciEditing.

Justyna Jupowicz-Kozak
CEO of Professional Science Editing for Scientists @ prosciediting.com