But that will definitely not be happening now. Ryan announced Friday night that Trump would not be attending their first campaign event together, a relatively benign fall festival planned for Saturday in Wisconsin. It was supposed to come less than 24 hours after The Washington Post's David Fahrenthold published audio via a hot mic in 2005 where Trump is recorded sharing incredibly lewd things about women. Now, Ryan's decision to drop Trump from the lineup is the talk of the 2016 election.
This isn't the first time Trump has made life difficult for Ryan within a 24-hour period. Ryan endorsed Trump in June. Literally the next day, Trump questioned a federal judge's objectivity, citing his "Hispanic" heritage. (Ryan was forced to call that "the textbook definition of racism.")
In fact, since endorsing Trump, we've calculated Ryan has had to denounce or disagree with the man he wants to become president an average of 11 days.
Back to Friday's headache for Ryan. Trump brushed off the hard-to-listen-to tape as "locker room banter." It will be very hard for Ryan to do the same.
Ryan doesn't just have one election to worry about -- he's got dozens. Democrats are hoping to take advantage of Trump's unpopularity in swing districts across the nation and eat into House Republicans' historic majority.
In response, Republicans have danced an exhaustive dance to hold Trump at arms length this election cycle. And for the most part, Hill Republicans' Hill Republicans' "support, but not really wink wink" strategy has been working -- so much so that Ryan had calculated he was safe to stand on a stage with Trump on Saturday, one day before a potentially make-or-break presidential debate, and following a pretty terrible week all around for Trump.
How quickly things change.
Now, the stakes are higher than they've ever been for Ryan and the Republican Party. It's very possible that this news is the moment vulnerable Republicans seize on to run as far as they can from their party's presidential nominee. Already one vulnerable Senate Republican, Sen. Mark Kirk (R-Ill.), demanded the party break from Trump. (Sen. Jeff Flake (R-Ariz.), who's not on the ballot this November, said as much earlier this summer. And we should note Kirk has already unendorsed Trump.)
Other Republicans have been walking a line so thin it's nearly invisible: Some, like Sen. John McCain (R-Ariz.) are running as a "check" on a hypothetical President Hillary Clinton.
Still others are denouncing Trump's comments but not him. Sen. Kelly Ayotte (R-N.H.) took heat earlier this week for saying she "absolutely" thinks Trump is a role model for New Hampshire children. She scrambled to put together a TV ad to walk back her comment even before Trump's 2005 audio became public. And on Friday, she was among the first vulnerable GOP senators to release a statement condemning the audio. More soon followed.
Senate Majority Leader Mitch McConnell (R-Ky.) issued one of the most strongly worded statements, late Friday: "As the father of three daughters, I strongly believe that Trump needs to apologize directly to women and girls everywhere, and take full responsibility for the utter lack of respect for women shown in his comments on that tape."
That's the Senate. House races, by their more localized nature, are more influenced by the presidential election. And that's really the root of Ryan's troubles: No matter how carefully he tries to thread the needle between Trump supporters and the rest of his party, Trump can say or do or Tweet something -- even more than a decade ago -- that in one instant smashes Ryan's diplomacy.
What's even more agony-inducing for Ryan is that before this news, some House Democratic operatives were publicly questioning the effectiveness of Trump attacks in certain districts, even wondering whether Trump's out-there-ness might be working to Republicans' advantage.
That might still be the case; it's too soon to tell. But Ryan, as the standard bearer of the party, can't not be mulling over the political consequences of appearing or even associating with Trump with his lewd comments as the back drop. For the moment, he decided showing up in public for the first time with Trump wasn't worth it.
Ryan has his own political future to worry about too. If he wanted to run for president in 2020, you can bet Democrats would remember he shared a stage with Trump after hearing what Trump said about women.
And that's the cruel irony of this election for Ryan: Just when it seems like he's caught a break from Trump, he hasn't.