Five years of relationship, we have trust issues and I have not met his family

Hi,

I’m F31, and he’s M30. I’m lost and torn.

I’ve been with my boyfriend for five years. Overall, things between us have generally been good — we get along well, rarely argue, and our personalities are compatible.

In January, he moved to the East Coast because he didn’t like the West Coast and his family was encouraging him to return. Since then, we’ve been long-distance, though he visits me monthly.

Last summer, I found out he had been talking to other women and meeting two of them a few times. More recently, I discovered evidence of another situation — a woman transferred him money for dinner, and he took an Uber to her place. When I brought it up lightly, he didn’t acknowledge it.

At the same time, we’ve been discussing the future, including marriage and eventually meeting his family. But I’ve never met them yet, and he has said they don’t currently support our relationship.

I’m feeling unsure about how to handle the combination of long-distance, trust issues, and uncertainty with his family. Any advice or insights on the situation is appreciated.

TL;DR: Been with my boyfriend (M30) for 5 years (I’m F31). We’re long-distance now. I’ve caught him talking/meeting with other women in the past and recently found more suspicious evidence. We’re also talking about marriage, but I haven’t met his family, who don’t support our relationship. Looking for advice on how to handle the trust issues and future planning.