When Should I Stop Counting?

I think I'm on date 5 now. Yes, I am counting the last meet-up as a date because I wouldn't categorize it as a non-date. Besides, there was a sleepover.
Date 5 was scheduled after dinner the week before and I was already thinking of ways to rearrange my schedule so I could maximize time spent together. Another Sunday date, I knew I'd have to fit in football so I opted for the afternoon.
A totally awesome friend of mine offered Chicago gourmet tickets (she is amazing) so I actually skipped watching another Ravens loss to head to the event. I had hoped to get the man in as well because I knew he'd enjoy lots of food and wine. I convinced him to head downtown and even managed to get him into the event. I was a bit nervous because this would be THE first introduction to any of my friends and I wanted him to be liked.
Upon meeting my friend, he really didn't say much and we ended up rushing around the event before it closed. Maybe I'd have liked him to spent more time by my side, but he'd wander to other stands without giving me a heads up. Is this our first fight?
I let that slide and enjoyed the copious amounts of free flowing wine. Small samples, I assure you. Post-event, we headed to a trendy hotel spot and cozied up on a couch with a great view. Then he suggested we take a picture. Wait, what? I'm normally the paparazzi for any occasion and I was shocked when a man suggested we take a picture on his phone. I over-read the situation like any sane girl would do. He must really like me.
Add another glass of wine and I boldly asked if he'd been going on more first dates. No. Jokingly, second or third? He paused. Shit. He hesitated some more. I went into grill mode. Who/what/where/when? I mean we did just take a picture. Actually, the conversation wasn't as tense as it seems though I did ask him to be upfront and honest about things. I had told him I'd gone on first dates so I expected the same level of honesty. No, I'm not ready to make it official, but I'd like to know if he's getting to that point with someone else. Further more, I said I'd want to know if he was sleeping with people because...gross.
Luckily, the wine had kicked in so I was able to move on pretty quickly. The night did turn out to be a lot of fun and he even commented that he'd miss me when he'd go on his upcoming European trip. Very sweet.
I woke up the next day with mixed emotions clearly due to the mixed messages I was given the entire day prior. Did I still like him? Yes. Did I go troll match for another date to keep my options open? Of course.