No, you cannot date Yuffie in Chapter 8 on a first playthrough in Final Fantasy VII Rebirth. To date Yuffie, you need to have a strong bond with her, which requires several steps and interactions throughout the game.

Steps to Date Yuffie:

1. Complete Specific Odd Jobs:
– Yuffie is attached to several side quests. Completing these side quests will increase her bond level.

2. Perform Synergy Skills:
– Use synergy skills with Yuffie in battle. Unlock skills for both Yuffie and Cloud to enhance your bond.

3. Choose Best Dialogue Options:
– Make sure to choose the best dialogue options when interacting with Yuffie. Selecting higher-starred options will improve your bond with her.

4. Main Story Beats:
– Pay attention to specific main story beats where Yuffie’s interactions are crucial.

5. Skywheel Date:
– By the time you reach Chapter 12, your bond with Yuffie should be higher than with other party members for her to accompany you on the Skywheel date.

Timing:
– Yuffie joins the party in Chapter 3 but does not become a full-fledged party member until Chapter 6. The Skywheel date with Yuffie occurs in Chapter 12, which means you need to build up your bond with her significantly before then.

In summary, while you can start interacting with Yuffie early in the game, dating her specifically requires a strong bond built over several chapters and specific interactions. Therefore, it is not possible to date Yuffie in Chapter 8 on a first playthrough.