Is it possible to have a great relationship with someone who is really insecure in relationships?
Washington, D.C.Every kind of relationship is possible, apparently, so I'll say it is -- especially if your favorite pastime is reassuring someone that yes, you did just go out to get milk and not to conduct a 10-minute torrid affair.
Cartoonish, maybe. But insecurity seems to reduce a couple to having only three conversations: 1. Defense of their actions. 2. Petty disagreements arising from being constantly on the defensive. 3. Mindless chatter about the one or two superficial topics they can safely talk about without starting a petty disagreement or having to defending their actions.
Relationship greatness comes when both of you grow far enough out of that stage to trust yourselves, because only then can you trust each other. And that's when you start talking about something other than trust.
I have been dating a lovely lady for two months. She is great, but, other than making dinner for me at her home occasionally, she never volunteers to pay when we go out. We both have good jobs with good incomes.
In these modern times when both sexes usually have jobs, I see little reason for the male to always pick up the tab. I am going to have to bring this matter up for discussion. Do you have any suggestions on how to handle this?
Handle it like just about anything else -- with care, context and a helmet.
First, figure out if this issue is a relationship-breaker. If a woman's belief that the man should always pay is, on its own, grounds for you to reject a woman, then, yes, you must bring this up. If it's an irritant easily justified by sparkling companionship, don't bring this up.
For what it's worth (about one-tenth of a caramel latte, I think), my opinion is that it's a deal-breaker. Granted, it is generally understood, and fair, that the person who invites someone out should also pay. But it is also generally decent for the guest at least to offer -- at which point the host refuses and everyone's happy with the early courtship routine.
It's when the early courtship gives way to seasoned companionship that context comes in. At some point, a woman who shares your views on modern times is going to feel uncomfortable watching you pay and pay. Likewise, a woman who doesn't share them is going to have other habits and mannerisms that conflict with your egalitarian bent. And the third case -- an oblivious woman won't have noticed who's paying for what.
Figure out which woman she is and choose your approach. For someone whose views otherwise align with yours, philosophical conversation ("I'm happy to pay, but it bothers me that you don't offer"); for someone whose views ultimately rub you wrong, second thoughts on pursuing her; for someone oblivious, "What say we split the check?"
Even with care and context, all three approaches could go sour -- an inevitable, valuable risk in getting to know someone. Which is where the helmet comes in.
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