Alpha Mail: should I stay or should I go?

PR writes to ask about the wisdom of proposing to his girlfriend:

I'm needing some advice about what to do about my girlfriend and you seem to be the best option at the moment. I'm 19 shes 20 and we've been dating on and off for 3 years now. Her grandmother( who she trusts the most) has had at least 3 divorces and her mom is probably bipolar. I've been the one to call things off with her the times that we did split up. I called things off with her because she became increasingly disrespectful and mocking as the relationship progressed. I would get sick of it and break it off with her. My gf and I are once again in a simliar position and right now she's pushing me to marry her in spite of the fact that I cannot find work and am probably joining the Air Force for work. With all her family history and the state of the family court system I'm more than a little hesitant.

Well, let's begin by simply counting the red flags.

1. She's older. Not the biggest deal, but marriages tend to function better when the husband is older than the wife.
2. They've been dating "on and off". So, the mutual commitment simply isn't there.
3. Her grandmother has three divorces.
4. Her mother is probably bi-polar.
5. She has a history of bad behavior once she becomes comfortable within a relationship.
6. She's pushing him to marry her.
7. PR doesn't have a job.
8. Military wives are notorious for their unfaithfulness.

I don't think PR has to worry about the state of the family court system. I wouldn't recommend any man marry a woman with more than one or two red flags, three at the absolute most if she has sufficient - what do we call the converse, green flags? Yes, green flags it is - strong positive indicators that directly compensate for them.

Point five is probably the most telling. Women's behavior NEVER improves with marriage. It always gets worse, in part because under the current legal regime, the leverage has shifted to the extent that the average woman now appears to believe that her wedding ring comes with a government-sanctioned veto over her husband. But that isn't the only factor, as there is also a tendency that PR has probably already observed, which is that women tend to treat those close to them rather worse than they treat complete strangers. The closer the relationship, the more a woman tends to believe that the other party has a moral obligation to put up with her behavioral extremes.

This is why it is so important that a woman's behavior is exemplary before marriage. Since she's on what PR knows is her best behavior, he has to expect that she won't be able to reliably maintain it once they are married. So, based on what PR is saying here, I would not hesitate to run, not walk, for the nearest Air Force recruiting center, sign up, break up, and refuse to leave a change of address.

I suspect PR already knows what he should do. He wouldn't be asking the question otherwise. My answer to him is this: you already know you would be mad to marry her. So, do the right thing and end it with her now rather than inflict additional pain on her by permitting any false hope of an ugly and unhappy future together.