He struggles to say what he feels

My boyfriend is a great person to be around but can’t communicate when we aren’t together. He can’t text or say what’s on his mind, and it becomes frustrating because I have to constantly try and guess what he’s feeling or thinking. When I tell him this, he always deflects it, and I forgive him because there’s nothing wrong with our relationship when we’re together. I worry about it only when he’s not around because it means I will have to constantly do the heavy lifting for us both. If this is what he will always be like, how will our relationship evolve? Should I assume that this is not someone I should consider spending the rest of my life with?
Communication is a learned skill which means it can be taught and improved upon. Whether it happens depends upon one’s will, and ability to recognise its importance in a relationship. If your boyfriend shrugs off your concerns, he isn’t taking this relationship very seriously, irrespective of how great he may be in person. Being able to maintain a relationship goes beyond physical proximity because both partners also have to be emotionally connected. Ask him what he thinks about a future with you, and what he is prepared to do to make it happen. If he can’t work on better communication, you will not be able to do the work for you both after a point.

Should I be concerned that my girlfriend is extremely stingy and doesn’t ever pay for our dates?
If it bothers you, it’s a problem, and you should definitely have an honest conversation about it. Not addressing it is a bad idea because you may want to be the bigger person today but will be unable to maintain that equanimity when times are tough. To talk about money is difficult, but it has the potential to ruin any relationship, which is why you shouldn’t shy away from telling her what’s on your mind. It may be awkward, but it is still necessary.
 
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