Is this cheating?

In January, my boyfriend went out with some friends. We had been having some problems so I told him to go and have fun, have some drinks with friends. He kept in touch throughout the night so I didn't really worry. I hate being home along though so I was sad. He came home around bar time which I expected. The next morning we were getting ready to go to breakfast and there was an open condom wrapper in his car without the condom. He swears up and down nothing happened but a make out session (even to this day). I obviously find this way suspicious but whatever. I chose to trust him. We ended up conceiving the day I found out he cheated on me which was awful... even worse that the pregnancy ended in a miscarriage at 11 weeks.

Then last Wednesday, he lies to me and says he's on his way downtown when really he was parked at a restaurant. I told him I knew he was there. And he confessed and said he was meeting a long time friend "Haley," who's husband is beating her and she's pregnant and has a son. So then, I looked at his Facebook friends for a Haley annnnd weird enough, there was a Haley we had just met at my friends baby shower who is in fact pregnant and has a son. He did meet with her. He says he had no intentions of doing anything with her. She was depressed, he's depressed, she's lost a baby and so have we, and he just wanted someone to talk to who wasn't me. Which I understood..... until I read the messages. He basically asked her if she was looking to move and needed a roommate, called her gorgeous, and gave her money because she's broke. He also offered to buy her and her son lunch.

We got engaged on Mother's Day and have been together for almost 2 years, so I want to think he's not dumb enough to mess anything up. He's been engaged before and the last girl cheated on him with his boss a week after he proposed so he definitely knows what it feels like.

I just need advice/opinions (weird right?) on whether the second scenario is cheating or not.