I'll admit that I like it when the guy always insists on paying as opposed to the ones who are happy to split the check. My rule of thumb is to offer. Times have changed and I don't believe we should sit on our high horses and expect to always be taken care of. Some guys will still not let you pay. If you're lucky to meet someone like that, good for you. If not, try not to judge the guy poorly.
I have found that almost every guy will cover the first date. I think that's is good enough. At least he's chivalrous enough to try and make a good first impression. The ones who don't offer on the first date, get a ding in my book. Chivalry should not be completely dead even though women are good earners nowadays. So first date coverage is bare minimum. But after that don't get too hung up on him always paying. In talking to men about this, many of them feel like they are being taken advantage of because there are plenty of women will sit on their high horse. Chances are, he's been on a fair number of dates and it can get expensive to always pay. So try and be a little fair after the second date and either alternate or preferably go dutch.
Now one problem I encountered is that I often had a smaller share of the bill. For example, I don't drink and the guy I was with did. I also was uncomfortable paying for his alcohol. He should recognize this if he's a good guy. He should be appreciative that you are willing to split or cover the check. But if he consistently consumes more than you, he should recognize that and either cover other costs like movie tickets or taxi fares or pay the tip or some other option.
If he doesn't do the right thing, don't hesitate to tell him that you'd rather split the bill differently. If he doesn't get the picture after your graciousness, then he's probably not a keeper.
Bottom line, the 100% chivalrous guys are great but try to be fair after the first date especially if you earn a decent living. It's OK for him to cover a little more but not for you too. There are exceptions, I met a guy who had a tough divorce. I really liked him a lot and I knew he was responsible and would get back on his feet. I probably eventually took on a little more than my share after a few months. But by then we were past the 'courtship period' and I was OK doing that because I knew he was recovering from a tough situation. I also knew he was a keeper and he treated me so well in other ways that money became less of an issue.
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