I have this aspect both with my ex-husband AND with the fellow I'd like to date and who is one of my best friends ... but the relationship can't seem to get off the ground. To make it more interesting, I have a Venus-Saturn opposition with a fellow I dated for a few months in high school, and who then *looked me up* 30 years later and tried to pursue me (I ran, ran ... there was also a Venus-Pluto opposition there, and several other difficult aspects ... very classic "unrequited"). In both the case with my ex- and the current guy, I'm the Saturn, they're the Venus. With Stalker Dude, I'm the Venus, he's the Saturn.
But in any case, I've experienced various manifestations of this aspect, so I can share what I've experienced.
First, the ex- and I had not just this aspect, but also a Venus-Neptune square, but both our Mars were conjunct, leading to a certain magnetism. So (as always) ONE aspect alone does not define a relationship. But with the marriage, we were together 23 years total, 20 as married. I look at the synastry and sometimes wonder HOW we got together or lasted as long as we did! Low compatibility score (something like 14!) ... but ... 23 years. The last 10 at least were NOT happy. We kinda felt chained, I think ... and that's Saturn. Duty. Yes, I'd say his Venus felt "squashed" by my Saturn. What we wanted in a relationship, and our basic personality types, didn't match. He's a shy extrovert, I'm a not-shy introvert. I'm very happy on my own, and NEED that -- he needed a completely different level of activity, action and togetherness.
One manifestation of Venus-Saturn square is that the Venus person is initially enamored of the Saturn person, but slowly, the passion cools/dies and the Venus person feels constrained, as if in a cage. The Saturn person may be partially or mostly unaware of this, and unable to meet the needs of the Venus person. That sums it up pretty well, actually. Classic "irreconcilable differences." We should have stayed friends.
Now, the OTHER guy ... we actually have a very HIGH compatibility rating (31 or 33, depending on how you want to count orbs). We also have a couple of the classic "soulmate" aspects. BUT ... we can't seem to get into a relationship. I'm older than him ... and yes, I'm the Saturn person. There are other "real world" constraints on the relationship. So despite some absolutely splendid synastry aspects -- that Venus-Saturn square seems to just KILL potential. I'm starting to think it's never going to go anywhere.
BUT if it did, I also think it has the potential (here's the karma) to do some HEALING. I couldn't manage the Venus-Saturn with my ex- ... with the other fellow (who's my best friend), I DO think we could manage it *because* of the positive aspects between us (and the lack of hard Neptune aspects which tend to deceive/bemuse/muddle the waters).
The thing about squares is that they're TEACHERS. We have to learn to manage them. They take maturity. When young, they can be SO frustrating. But as we age, we get better. I was a kid when I married my ex- (21). Now, I'm 47. I learned a lot. If we could just get the thing off the ground, Saturn stabilizes and a square from Saturn teaches. I know what to look for, beware of, and how to manage it. Squares are fricative and FORCE you to manage them (or they manage you). And frankly, that's what marriage is like. They take WORK. It takes two people to make a marriage, but only one to break it. Learn to manage Venus-Saturn and it'll be the bedrock.
Easier probably to have a sextile or trine, but I think the conjunction and squares CAN be handled with maturity and awareness ... and enough other more "cheerful" aspects: like sun-Venus or moon-Venus aspects, positive moon or positive sun or sun-moon aspects, good Mercuries (indicating an ability to talk easily). Sun-Jupiter helps too. I point to these because sun-Venus is about real affection (not just sexual attraction), and good Mercury means good communication. Good Jupiter is cheerfulness/helpfulness. So all those will help counterbalance the "heavy" Saturn hard aspect.
Where I have my doubts (based not just on my experience but that of other charts I've looked at) is the Venus-Saturn OPPOSITION (or the quincunx too, which I don't really count a minor aspect). Here, I think the energies are such that they just kill each other, or are so on-off, they can't be easily managed at all, or even worked through well.
I've seen squares and conjunctions work long-term. I've not seen a Venus-Saturn opposition work long-term. Now, I've hardly seen everything (at all!), and I'm sure they do sometimes work, but I think it would require a LOT of other, helpful, extremely positive aspects.
Btw, with Stalker Dude, and the opposition, I just felt completely chained/constricted. But there are (again) a lot of other difficult aspects including Sun-Jupiter opposition (extremes), a Mercury/Pluto to Venus opposition, Neptune-Venus square and Neptune-Saturn square. So LOTS of things wrong there, very little good. To be frank, he creeped me out more than a little, seemed very manipulative (even though I'm the Pluto in the Venus-Pluto opposition), obsessed, and CLINGY. I'd say the "clingy" was some of the Saturn. Saturn NEEDS Venus.