Mid 40s Boyfriend Too Cheap for Mid 20s Model Girlfriend

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DEAR MIDLIFE BACHELOR:  I am in my mid-twenties and I am in a relationship with a man in his mid-forties. We both have never been married but are marriage minded. He has made it clear he wants to settle down and start a family.

I am having issues with out relationship because I feel like he wants the benefits of having a younger girlfriend without the responsibility of one. I returned to college to get my degree after having a successful modeling career. Because of this, I don’t have the income I use to have.

Obviously he is at a different point in his life. He has a very successful career and is stable. He pays when we have dinner and we went to a resort for a weekend getaway. I am appreciative of this and always thank him. Recently my issue with him was relating to a more personal nature. I needed to visit the gynecologist and get an Rx for birth control but I don’t have health insurance so I would have to pay out of pocket. I felt that because this was an issue that affects both of us, he should offer to help pay for it. When he didn’t, it bothered me so I decided to talk to him about it.


Basically he felt that it wasn’t his responsibility to take care of me and that I shouldn’t have to depend on him for medical expenses. He said he wants a 50-50 relationship and he doesn’t want someone trying to take advantage of him. When I asked him why he thought I was taking advantage of him, he said that I wasn’t but that it was a concern of his with past relationships.

I really like my boyfriend but I’m having a hard time accepting his reasoning. I feel like a 50-50 relationship would be for him to date another successful mid-forties woman – not a struggling college student. I don’t want to take advantage of him, that’s not why I am dating him. I’m an old soul and I prefer dating older men.

I don’t know what to do. I really like this guy but I feel like this is a deal breaker for me. I feel like I have a lot to offer in a relationship and want to be with someone who is more generous and wants to help me. Am I being unreasonable? I’m trying to understand why an older man would feel this way about a younger woman.


Thanks for writing in. Without question, I believe I speak for the majority of the midlife bachelors of America when I say that your boyfriend should thank his lucky stars for having the opportunity to date a mid-20s former model.

In my mind, he should be more supportive of you because of your age and employment status. The fact that he is not is a warning sign … he could very well turn out to be cheap in other respects, and maybe you just haven’t seen those yet. To be fair to him – you might talk with him more, and explore how other women in his past have treated him … he may have been severely taken advantage of. I think it would be helpful for you to understand more about his history in this regard – so take some time, and try to get him to open up about this. It could be that he doesn’t mind helping out – it could be more of THE WAY YOU ASK for help … insist versus suggest versus something else, etc. In other words, he could simply hate it when women ASSUME things. To me, it doesn’t sound like you have all the necessary information yet to make any permanent judgment calls about the relationship.

Does he know how lucky he is to have a 20s girlfriend who is a former model? JEEZ that’s hot. He should think about that! Speaking for the rest of us mid 40s guys – most of us would go overboard to make you happy, especially if you really want a long-term relationship. So from this perspective, your boyfriend might be whacked (crazy).

You do sound like very intelligent woman – and I’d say that you have a lot of options if this guy doesn’t work out. I wouldn’t jump to any quick conclusions because you seem to have an emotional investment in this guy – so after you talk with him more, take your time when thinking about all of this, and then build a case in your own head as to why you should stay with him, or not. In my own personal life, I have always tried my best not to make quick or rash decisions – I’ve found it is usually better to take come time, and think things through. And so that is precisely what I recommend that you do.

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.