It's like a blind date, with one of the partners hemming and hawwing over whether this is really a good idea.
That would be Miikka Kiprusoff, the Calgary goaltender, who knows the Maple Leafs would like him to twin with James Reimer and give the young Toronto squad some much-needed post-season experience.
GM Dave Nonis pitched Kiprusoff on the idea of coming to Toronto on Tuesday, and then began discussions with agent Larry Kelly Wednesday night on the possible parameters of an extension.
That would have to be a gentleman's agreement, as an actual extension to Kiprusoff's deal can't formally be done until the summer. It's likely the Leafs would be willing to pay Kiprusoff in the neighborhood of $5.5 million for one more season after his current contract expires after next season.
Nonis and Kelly are expected to talk again in the hours before today's 3 p.m. NHL trade deadline. It's clearly a trade Nonis wants to make happen - probably for mid-round draft pick or a conditional pick - if the extension money is reasonable, assuming Kiprusoff will come.
If he does, the expectation is that the 36-year-old veteran would share goaltending duties with Reimer, rather than come in as the annointed starter. That's a very different scenario from acquiring Roberto Luongo, who because of his contract alone would come east as the new No. 1 netminder for the Leafs.
With 10 notable players moving over the past seven days, all is currently quiet on the NHL trade front, with movement expected to kick in shortly after noon. Last year, the first trade on the final day occurred at 10:35 a.m., with Andrei Kostitsyn moving to Nashville from Montreal.
We all know how that turned out for the Predators. So maybe it's better to wait until lunch.