Dear Jessy:

I like crystal clear.

“I might ping him end of this week as its also his birthday so it might be a good conversation opener.“- I would wish him a happy birthday in just the same way you worded it when you were together,  minus words reserved to an ongoing romantic relationship. He contacted you at the beginning of this year, after 2 years of no-contact, because (I am guessing) he missed you as he remembers you, so give him what he remembers: the same wording, same sentiment, be as friendly as you were before (minus the romantic).

For a conversation regarding the changes in his lifestyle and personality in the last 2-3 years, you can start with something that would be easier for him to answer (as opposed to asking him about new experience dating, and such):

“he goes hiking now (which he resisted to do with me back home earlier )“- you can ask him (unless you already did), what made him like hiking in the new country, which he disliked doing in the home country.

To encourage him to talk more, be friendly, come across curious and interested in hearing more from him, as a friend.  If he initiates romantic+ talk, don’t go silent, as before. Instead, ask him more personal questions: not in an interrogative, negative tone or wording, but in a friendly (not romantic) way.

You have to gather information first, to get to know him anew, before you decide which way you want to go with him. That’s why a friendly, inviting attitude is needed. You can tell him- sometime after talking- how exciting it is for you to get to know him again.

If you started talking with him in a romantic way, it’s likely to be awkward for him to talk about his dating experience in the last few years, but if you establish a friendly, curious attitude, he is more likely to tell you things he wouldn’t otherwise.

anita