I love time travel stories and have rad a lot of them. I've written a few too. The issue, as I understand it is that you have chronological time which is what Ryan experiences but you have a folded time which is what Andy has lived. Effectively we have two frames of observational reference (Einsteinian relativity concept) while we are used to treating time as a fixed frame of reference (which it actually is not).
By age
The Time Travellers Wife deals with this by giving you the age of each character in the chapter. This helps us get a feel for where each of the two characters are along their own timeline. You might wish to do that.

Chapter Six: Andy 51, Ryan 26

As there is a single loop, these numbers will increment at the same rate after the journey back.

Chapter Seven: Andy 52, Ryan 27

But you would also have something like this for pre-change time.

Chapter Three: Andy 27

Personal timelines
Another approach might be to reference the time and the frame of reference.

Chapter Nine: June 7th 2012, Andy's time

and the second timeline something like this:

Chapter Ten: June 7th 2012, Ryan's time;

Alternatively:

Chapter Ten: June 7th 2012, Ryan's time; Andy +25 years

By Epoch
The choice is partly down to how and what you want to express. If you want to talk about pre-change and post-change timeline, then use the jump as an epoch.

Chapter Nineteen: June 18th 2014; 24 years, six months, four days, three hours post change.

or just express the epoch in hours

Chapter Nineteen: June 18th 2014 +214,719 hours

This works well for the old timeline too

Chapter Twenty: June 18th 2014 -184 hours

or

Chapter Twenty: June 18th 2014, 184 hours before Andy changed everything

As long as you are clear...
Pretty much every combination of those ideas would make it very clear to me, if I were reading this story, which timeline I was reading. I honestly cannot pick a favourite. Speaking of which, I really do want to read this story.
As a side note, this could be a situation where a prologue could be powerful and effective. Generally, I hate prologues as they do not work and should be banned but, every now and then, a writer comes along and breaks the rules and it is wonderful. Break the rules as often as you need to - but do so knowing that there is a rule and that you are deliberately and purposefully breaking it.

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