What are some signs that a guy is enjoying your company?

The most useful thing to track is what he introduces without you prompting it. A guy who enjoys talking to you will mention something from a conversation two days ago, ask how the thing you were nervous about turned out, or send a photo of something he thinks you would find funny. Those messages tell you he is holding onto the conversation between contacts, which is different from just answering when you write. Count how often the thread is started by him over a week or two. If the ratio is roughly even, that is a healthy sign. If you are always the one opening, that tells you something too, even if he is pleasant when you do.

Also notice the questions he asks. Generic questions like how was your day come from politeness. Specific questions about a detail you gave him show he was paying attention. The difference is usually obvious once you start looking for it.

Enjoying someone usually shows up as effort toward the next meeting. Look at how he talks about getting together. Someone who likes you will name a day, suggest a place, and if you say no to one option, he offers another instead of dropping it. He will also let you know when he is free, instead of asking when you are free and then waiting for you to decide everything. Vague talk about we should do this sometime, with no follow-through after a few days, usually means he likes the idea of you more than he is organizing time for you.

If you have had one plan fall through, watch what happens next. A person who enjoys your company will reschedule with enthusiasm and ideally a concrete new option. Someone who was lukewarm will apologize, say let's pick a time soon, and then let it sit.

Text can hide a lot, so the in-person read matters. Notice whether he stays past when he said he had to leave, whether he moves closer or turns toward you when you talk, and whether he is still engaged in the last twenty minutes of a date. People who are not into it start checking their phone, wrapping up stories early, or suggesting you both head out. People who are enjoying it lose track of time and tend to ask for another round or suggest a walk.

Also watch whether he shares things about himself that he did not have to. Telling you about a family situation, a job he is unsure about, or an old story he looks slightly embarrassed to tell is a sign he is comfortable with you and wants you to know him.