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From personal experience alone I would have to say depending on how serious the relationship is I would in my power not try to make him feel like less of a person due to the money issue. There are many places to go that do not require money. For example find a park near an airport and have a picnic dinner - even if it means eating in the car. Make a deal you bring dinner this time, he brings dessert. I am sure there is some tourist web site that can help you find places such as that. Also a good thing about not going out, and staying in and renting movies and such is that you won't be in such a crowded environment and it will help you two to become closer. However if the situation does arrise that you need to go someplace that is fancy instead of "splitting the bill" you can say before hand "hey how about I grab the check this time, and if you want you can catch it next time" and if you really want to make this work next time, find someplace cheaper to make it easier on him. Hope this helps!

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Q: If you feel guilty that your boyfriend makes less money than you do should you split the bill with him when you go out?
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