Anonymous wrote:

Anonymous wrote:Sext him some nudes.


Kidding. You've know each other too long. Be upfront. Billy, this is fun and all but I can't continue down this path while you are in another relationship. Feel free to give me a call if things don't work out. If the timing is good and I'm unattached, I'd be open to a date to see if this chemistry is real.

Yep. This is what I would do too.

I agree. That's where I'm at.

-OP

Anonymous wrote:Sext him some nudes.


Kidding. You've know each other too long. Be upfront. Billy, this is fun and all but I can't continue down this path while you are in another relationship. Feel free to give me a call if things don't work out. If the timing is good and I'm unattached, I'd be open to a date to see if this chemistry is real.

Yep. This is what I would do too.

Sext him some nudes.


Kidding. You've know each other too long. Be upfront. Billy, this is fun and all but I can't continue down this path while you are in another relationship. Feel free to give me a call if things don't work out. If the timing is good and I'm unattached, I'd be open to a date to see if this chemistry is real.

She's been available a little less than one week. How soon is he supposed to dump this woman?

The keeping mum on details is odd. Maybe he wants the cake and to eat it too. Maybe he's lying. Or maybe he wants to make sure OP is in the bag first. Few ppl would circle so far back to a true friend for a cheap flk

He sounds like he is not 100% sure if he wants you now that you are available because trust me if he did he would have dumped his girlfriend already & taken up w/you.

And he hasn't.

He likely was taking his sweet old time deciding what he wanted which wasn't even close to fair for both you AND his girlfriend.

What concerns me is that if overall he was a good friend/person overall then how could he flirt w/you the way he did while having a girlfriend....??!

And why is he keeping mum about her??

Trust me, any guy who would flirt inappropriately w/another woman while in a relationship is definitely not even close to being a catch in any way, shape or form.

I promise.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:How long has he been dating this woman? You also have to remember that the two of you are now completely different people.

I don't know how long they've been dating. When I asked for details he was mum so I left it alone. I was pulling teeth and I ended up with nada so I dropped it.

Last week when I told him that I had a lunch date he asked for all the details and insisted he must meet the guy before I could proceed. He was being a protective friend. That's the only reason I felt comfortable demanding to know about his situation.

I'm getting red flags all over the place here.

No worries. I'm done.

Backing off.

Giving him/them their space.

We can continue to be friends from afar with the annual birthday, Mother's Day, Merry Christmas and occasional "How you doin'?" texts. No more late night phone calls into the wee hours of the morning. No more platonic friend dinners. Clearly, I got red flags too.

Anonymous wrote:

Anonymous wrote:How long has he been dating this woman? You also have to remember that the two of you are now completely different people.

I don't know how long they've been dating. When I asked for details he was mum so I left it alone. I was pulling teeth and I ended up with nada so I dropped it.

Last week when I told him that I had a lunch date he asked for all the details and insisted he must meet the guy before I could proceed. He was being a protective friend. That's the only reason I felt comfortable demanding to know about his situation.

I'm getting red flags all over the place here.

Anonymous wrote:If there were ever two peas in a pod it is you two!!

LOL

Anonymous wrote:How long has he been dating this woman? You also have to remember that the two of you are now completely different people.

I don't know how long they've been dating. When I asked for details he was mum so I left it alone. I was pulling teeth and I ended up with nada so I dropped it.

Last week when I told him that I had a lunch date he asked for all the details and insisted he must meet the guy before I could proceed. He was being a protective friend. That's the only reason I felt comfortable demanding to know about his situation.

Anonymous wrote:If it doesn't work out with this chick then he'll date you. He is keeping his options open. He might f*** you. Don't do this bc then you'll only ever be a side piece or he'll gradually stop talking to you completely. I would stop being as available. If he breaks up with the other girl then he can call you. Maybe you'll be single.

OP here.

Yup! That's where I'm at. I really value our friendship. It has been platonic and we really respect each other as people. He really is the nicest, greatest guy. He was back then and since reconnecting I've been feeling him out to see if he's still the same sweet genuine person. I'd rather remain friends than have things turn weird and awkward by having sex with him only to have him end up with someone else.

I do plan to respect the boundaries (that's just who I am), continue to date and perhaps the timing will be better next time. If not, oh well. There are other fish in the sea.

If it doesn't work out with this chick then he'll date you. He is keeping his options open. He might f*** you. Don't do this bc then you'll only ever be a side piece or he'll gradually stop talking to you completely. I would stop being as available. If he breaks up with the other girl then he can call you. Maybe you'll be single.

If there were ever two peas in a pod it is you two!!

How long has he been dating this woman? You also have to remember that the two of you are now completely different people.

It seems you think you'd win the competition for Billy's affections. But if you move in too fast, you also stand the chance of confusing him and if that's the case, at some point he may back off to get clarity, and then you may feel foolish. So let go and let him figure out what he wants. He can pursue you, too.

"Billy" and I knew each other on and off since HS. We fooled around a bit in college (kissing and touching) but never had sex. We graduated, married other people and lost contact.

We reconnected 15 years later when he found me on social media. We were both married with children and didn't so much as exchange phone numbers. Fast forward a few more years, we're both divorced and our children are grown.

We went out to dinner as old friends a few years ago. He asked about becoming a couple. At the time I was going through a bad situation and didn't feel the time was right to be involved with anyone. (I was also a bit taken aback that he jumped in so quickly based on who we were in our teens and 20s. I thought that conversation should've happened after a few more dates.)

Fast forward to now--

I saw "Billy" last weekend. My bad situation is behind me and I ready for love. More importantly I am ready for love with "Billy". There's just one problem. "Billy" has been dating someone.

He was a perfect gentleman last weekend, but we've talked on the phone every night since then. He's inquired about my relationship status, presented the question about us being a couple and happened to mention that he is currently dating when I asked. I thought he meant "dating" in the same sense that I'm "dating"--going out for coffee or lunch with a nice guy or two but not committed. We've been quite flirty and inappropriate in our conversations with one another. He even brought up our make out sessions in college.

Once I felt interested in pursuing a relationship with "Billy" I decided to get clarification on his relationship status. He said that he is seeing one person, and it sounds like a relationship. But he says he's still trying to figure out if she's the one he wants. At the same time he keeps telling me that I'm still sexy and attractive to him. I told him that I feel the need to respect his relationship but that didn't stop me/us from continuing to be inappropriate.

So now I'm wondering how or IF I should proceed with him. We are really good friends first and foremost, which is why he allows me to get away with being inappropriate with him. On the surface it's two friends being silly with each other. But we both know that we want each other.

I want to just let it go and let his current situation play out. Then again, I want to just go full speed ahead based on our history and friendship and let him yell "Uncle" if I get too close for comfort.

We're both in our mid-40s and yes I know I sound juvenile, but love and relationships will do that to a person.