Need Some Dating Advice (from adults, please)?

Hello Everyone,





It is weird. I have no problems talking to guys about anything or hanging out with them, even the ones I like. The big problem I have, is asking a guy out or letting them know I am interested in them. I just cannot do it.





But, added to that, is the fact that I am uncertain if the guy I like is interested in me. He has given me some mixed signals, and there are a few other things to throw in there that make me wonder. I am not sure if these signals are sincere ';flirting'; or if he is just joking with me in these ways because he considers me a really close friend.





Just some background information first. I have known him for a little over a year. Close to two years, actually. We both go to the same college. We both have a bunch of mutual friends. We also hang out a lot together. He is two years older than me...and we are both a little older than your traditional college student. I am 26, he is 28. But, he is an international student.





We hit it off pretty well in the beginning as friends. We always chit-chatted and talked a lot when we saw each other. At that point, I was not interested in him romantically, and I think he felt the same. At that point, I was interested in someone else.





The guy I like now, he is a really great guy and loves to sit with his friends and listen. He's always there to offer advice, and he has a really good head on his shoulders. So, when I liked this other guy, we talked about this. When things did not work out with this guy, we talked about this to. We also talk a lot about our families and our personal life. Just to give you an idea of how good of a ';friend'; he is, my roommate jokes around and says he is like a ';sister'; because she can talk to him about anything and tell him anything.





Lately, he's been flirting with me, or what I think is flirting. Here are just a few examples.





Every time we hang out, we playfully pick on each other. There are times we play wrestle, both of us have started them, and I usually lose (lol. He is a personal trainer and served in the military). There are a lot of times we have shared jokes or picked on each other in ways that have subtle sexual over tones. Also, we ask each other to hang out a lot. Most of the time, he asks me, but I do ask him, too. Half of the time, it is just him and me. The other half of the times, we're out with friends.





Back around February/March, he was talking to me and told me that if neither one of us had found someone by the time we both graduated college, we would just get married. He still jokes about it even now.





One day we were having coffee. A lady came into the coffee shop with her 1 1/2 year old son. We both played with the little boy. As he was leaving I said ';He is so cute!';. My guy friend asks me ';Do you want a baby now?';. I told him ';Kind of, but I think I'll wait';. Then, he jokingly tells me ';Let's go back to my place';. He caught me off guard, so I just told him ';Don't you think we could wait until we finish college?';. He just smiled at me and winked.





Last night, me, him, and four other friend were hanging out at his place. We had some drinks and were smoking hookah (flavored tobacco for those who do not know what this is). Before we even started, he joked about the baby thing again. Then I made a remark that I was not going to drink a lot so my clothes would stay on (just I joke, I do not really strip when I've been drinking). He jokingly tells me to drink more. Later in the evening, I was getting a little tired, and he offered to let me nap in his bed. I told him I wasn't tired. He then jokingly tells me that if I go, he would follow me in. Later in the evening, I do end up crashing (before everyone else leaves). I slept in his bed, he slept on his couch. When I woke up in the morning, he tried to convince me that I had stripped last night. I told him I know I did not. Then he jokingly tried to tell me that if I had, he would have taken advantage of me. Later in the afternoon, he drove me home, but we stopped to get coffee on the way to my place. We also had lunch today (just me and him), and dinner tonight (with three other friends).





These are just a couple of numerous things. They all seem like he is flirting with me. I do have to admit I have developed a ';crush'; on him. And I would like to ask him out, or let him know I am interested to see what he thinks. But, there is a big issue (to me) that holds me back, other than my usual nervousness in doing this.





For one, he has had an interest in one of my good girl friends for the longest times. She is such a good friend that she is like a sister to me. She has no feelings for him, and she has told him this several times. Him liking her has not stopped him from dating in the past, but he still tried to get her interested. He will leave her alone while she is dating someone, but will be back to trying to get her attention as soon as she is ';free';. She is dating a guy from Germany now. The two have been dating for aboNeed Some Dating Advice (from adults, please)?
With due respect, your question is too long, it is intimidating to see such a long protracted post.





Remake it into a smaller one.