Courtship in SLOOOOW Motion

QUESTION: Hi Chuck and Garland, I am hoping that you can help me. I seem to be a great judge of character and can always tell when a guy is interested in me when I have absolutely NO interest in them. As soon as I become interested in a guy, I can't make heads or tails of him. So, here's my story. I have known this guy (we'll call him John) since high school. He was actually my Grad Night make out guy. We dated for a little while during the summer...and it ended for no reason that I know of. We never had sex. About 17 or 18 years later we met up again. Both of us were only a couple years out of a divorce. He has a daughter and I have 3 kids. We were both cheated on and clearly very jaded at that time. We had a great time, talked all night non-stop and ended at my door with a nice hug and a great kiss. Afterward, I got a couple of emails and then nothing. I understand why he didn't move forward at this time. I know that he just wasn't ready for anything. In retrospect, I wasn't either. About 4 years later, I started dating another guy (We'll call him JA), and shortly after we started dating, I found out that they (John and JA) were friends. I had no idea. During that time, we (me and John) were both very respectful and didn't email or talk during the short lived relationship with JA, we didn't really hug or anything when we saw each other, but we joked around a lot and finally the relationship with JA ended. It has been a couple of years again, and through Facebook, we are in touch again (me and John). We have hung out at group gatherings (one of which I put together). We chat (IM) for long periods of time once or twice a week and occasionally talk on the phone if for a particular reason but, never just to chat. We both love to hike and he asked me to join a volunteer group with him and his friend Jim. Outside of volunteering, we have gotten together a couple of times along with his other guy friends (Jim and Dean) whom John is really close friends with. Everytime he sees me, he gives me a HUGE hug, sometimes two. I don't really hug the other guys. He even met my youngest daughter and I met his when we went on a hike once (they are very close in age). My other two are much older and one of them has already moved out. Anyway, I have also hiked with Jim and Dean without John several times. I can tell that Jim clearly likes me and Dean has pried to find out if I was interested in Jim. Dean later asked me if I was dating anyone. The answer to both was no. We even talked about my failed marriage and being cheated on and I told him that I was tired of wasting my time with guys that I know are not going anywhere, that I prefer to date a guy with kids (as a common interest) and that I don't want to date...just to date. Dean asked a lot of questions, was it just curiosity? Do these guys talk to each other or do they get their info and keep it to themselves? In the meantime, I continue to chat (IM) with John. We jokingly bring up dating and marriage issues that other couples have (i.e. playing games, cheating, having a wall up after being cheated on) and vow that we never want to be involved in anything like that. Keep in mind that we never mention US being together. Then, one time he jokingly asked me what he would do without me and asked if I would marry him. He always calls me sweet names and tells me to have sweet dreams when we finish chatting. Recently, he told me that he "loved chatting with me". I told him that "I loved chatting with him too" and that he cracked me up. What should I make of all of this? Is he interested? Is he just moving SUPER slow and feeling me out first? Is he looking for reassurance that I won't cheat on him? Is he afraid to ruin the friendship? Am I reading way too much into everything? I just don't know. Thanks for your input.

CHUCK: It could be possible that John is just goofing around. But I think the greater possibility is that he is maybe now starting to realize what he's been missing with you. Here he's known you for the better part of 20 years, and your relationship has been largely platonic, but I think he's probably been thinking about how to change that status without making a fool of himself.

What could have changed his feelings? The fact that you've gotten to know his boys could have a lot to do with it. Here, you've spent time with him and them, and you think that you've seen some mild attraction from one, or both of them. I guarantee you that, by now, someone has asked John, "So what's the deal with you and her?" John probably hemmed and hawed for a little, then finally stated that you're just friends. And they probably asked him why. Then they suggested that he at least consider moving your relationship out of the friend zone. And since they are probably good friends and not creeps, they've laid back so John can make his move.

But that move is verrry sloow. So the question becomes, how do you feel about that? How do you feel about John? Can you see yourself with him? Think about that. One of the reasons John is probably going turtle-speed with you is because you already know his history (bad marriage, been cheated on, etc.), and he can't play any of that off. That could make him a little uncomfortable.

You've got a choice here. You could wait another 18 months, while John negotiates his next move. Or you could try to help him along, if you think you might be into him. If you're not the type to take the bull by the horns, and say "What the hell, let's see where this goes, John," then you need to make it easy for him to make that move. Subtly let him know that your feelings for him are no longer just platonic. And who knows? Maybe slow and steady can win the race.

GARLAND: Thanks for your question. Honestly I really don't know what is up with your guy John. Moving slow is one thing, but after almost 20 years I would halfway expect a guy to be willing to step up pretty quickly, I just can't see a guy meeting back up with you, hugging, watching you date is boy, no more hugging, watching you break up with his boy, restarting of the hugging, wasting another four years, more hugging, and tease from a potential new beau, still more hugging.

I just don't know.

He could be serious and want to start a relationship, but his slow start and timid approach to you makes me a little leery of a man with his 40th birthday in the rearview mirror who may be scared of hitting 50 all alone. I think you have to sit him down and see how he feels about you and see if he's using the years between you to solidify a special friendship or if he has finally accepted that you hovering around the perimeter of his life means that you are the love he may be looking for.

I wish I could give you more, but this guy is THE ONE with the best answer.