Following up on a comment on my earlier post, "The Domestic Violence No-Girlfriend Order":
It's true that, though quite unusual and, to some, shocking, this kind of alternative sentencing condition is not necessarily invalid. As the commenter points out, the offender could be sentenced to imprisonment instead, which curtails one's rights to intimate association even more severely. Even though a fundamental right is involved, it would be a short leap from applying strict scrutiny to such a sentence to applying strict scrutiny to prison sentences, and (whatever criticisms might be leveled at the use of imprisonment as a policy matter) no way are courts going down that road.
Rather, conditions of probation and the like are typically subject to evaluation for their proportionality and reasonableness in light of the offense, and it is on this basis that courts have found acceptable conditions that persons convicted of refusal to pay child support refrain from having children, most famously in the Wisconsin case of State v. Oakley.
Clearly, then, a condition of refraining from intimate relationships is not going to be per se invalid, and a clear analogy can be drawn from the procreation cases, where a drastic condition was imposed on chronic repeat offender to prevent the conditions for reoffending. Both chronic nonsupport and domestic violence are widespread social ills with high rates of recidivism that appear very difficult to deter through conventional means. And in either case, per Griswold v. Connecticut, the State is forbidden from any intrusive surveillance to enforce the condition; it will largely depend on the routine supervision of probation officers.
I wonder, though, how this is going to be enforced. What exactly does it mean to refrain from any "romantic relationship of an intimate nature with a female person"? Does this mean no sex? No going out to movies? No holding hands? No showing up at singles bars? No flirting? Is casual sex okay, but going steady off-limits? In other words, might there not be a vagueness problem here? (I don't think this is merely a theoretical problem either, as most people sooner or later would feel a need for some kind of intimacy and be sorely tempted to skirt the limits of such a condition.) And if it were rewritten to be more precise, just how broad a ban on intimate associations would be deemed proportionate to the need for specific deterrence? (And then there's the seemingly gratuitous specification of gender, which raises at least theoretical Equal Protection concerns.)