Fleischer Studios made many good to fine cartoons in the Popeye series (109 between 1933 and 1942, before Famous Studios took over all the way through to the late-50s), while liking a good deal of their work Popeye to me was one of their better series to feature a regular character. Speaking as someone who likes the Koko cartoons and pre-code Betty Boop. The Gabby, Stone Age and Animated Antics series don't do the studio justice.
'A Date to Skate' is from the series' best period (the late-30s in my opinion), yet it is not one of the best cartoons. While still enjoyable, to me it's a lesser Popeye cartoon from the year of 1938. This is not a Popeye versus Bluto cartoon, and another change of pace for Popeye, which are every bit as enjoyable and in a good deal of them even more so than the Popeye versus Bluto efforts. The premise is not an original one, so 'A Date to Skate' is on the formulaic side with few surprises going on, but it doesn't get too repetitive and has enough amusement.
On top of being pretty predictable, am going to agree that it does start off pretty dull and too much of the cartoon felt like set up. The thin story does take a little too long to get going, not much of the material is particularly funny (pleasant but not much more) and the pace is too on the restrained side compared to the usual wildness.
What agreed redeems 'A Date to Skate' is the final act, which is classic Popeye in the best way. Wildly paced, everything coming thick and fast without being rushed and hilarious. Some of the humour comes from Popeye's mumblings which is something of an art form in the Popeye cartoons.The climactic chase is the clear highlight. Popeye is very easy to like and is is amusing and he shares a charming chemistry with Olive, who has an equal amount of time on screen and with material just as good as Popeye's and some of her best actually from this period.
Regarding the animation, it is very good as always from this period. It's beautifully drawn and with immaculate visual detail, that doesn't ever feel cluttered or static, and lively and smooth movement. The music likewise, lots of merry energy and lush orchestration, adding a lot to the action and making the impact even better without being too cartoonish. Fleischer's direction is always accomplished and his style is all over it. Jack Mercer does a typically great job as Popeye, with him clearly enjoying the asides and mumblings the viewer enjoys them too. Mae Questel was the most prolific voice for Olive for good reason, with a voice that actually fitted the character design and personality.
In summary, rough start but the final act helps making 'A Date to Skate' worth seeing. 7/10