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I notice in the first pic that the social bubble in the top left says "Bebe thinks James is being flirty" - in the "being flirty" stage, not many interactions are available. If you keep flirting for long enough, the bubble will switch to "X thinks Y is being very alluring", at which point more interactions are available; and the next, and highest, stage, is "X thinks Y is being extremely irresistible", which enables all romantic interactions.
The same system applies with friendly interactions - at the "X thinks Y is ok" stage, you don't have, for example, the Friendly Hug or Express Fondness options; those become available as you move into "X thinks Y is being sociable", "X thinks Y is being friendly", etc stages.
At one of the later two flirting stages, I forget which one, you'll see the option to "Propose Going Steady" (if the other sim is single); this will give you the boyfriend/girlfriend marker. If you don't like that, there are a few hacks available which change it in some way, though I'm not sure exactly how.
What I lack in decorum, I make up for with an absence of tact.