Tried it, and they weren't even a Tridentine attendee, just a lady who goes sometimes and was homeschooled, but who wore a skirt or dress nearly everywhere (except sports and cycling), wore gloves and a hat at Mass and only received on the tongue, etc. We didn't get beyond initial conversations. When she found out my parish used "The Saint Michael Hymnal (considered somewhat traditional)" she thought I was bound for Hell.
I have a vintage St Joseph Daily Missal in excellent condition. I am not against wearing a veil to Mass. If I didn't live so far away from a Latin Mass, I would go on a regular basis....meaning every 4-6 weeks. ((I have an SUV and cannot afford the gas.)) The sacredness, solemness and beauty of the Latin Mass is unparallelled.
It's important for a couple to be able to attend Mass together. If either one finds the other's preferred worship stlye to be outright repulsive then I don't think it would work very well. For example, I couldn't stomach a charismatic service. I would still drive a half hour to go to a more traditional-looking Novus Ordo Mass over an uber modern one 5 minutes away (although I would prefer the TLM over either). I think that would lead to some friction with someone who prefers a less traditional Mass.
I find it difficult to believe that a preference about liturgical rites would curtail a loving relationship. We're all Catholic, right? The Eucharist is still the Eucharist.
That's because you're a reasonable guy who loves God instead of loving having your will be done in all things.
Unfortunately, for all too many of the Trad disposition, the MO is "my way or the highway".