What is he thinking?

[wappyboy]

I have never been sexually active; but just recently, I decided to give Craigslist a chance and hook up with a number of dads/bears. Since the premise of the hook ups is based on NSA action, I really don't have any chemistry with these guys outside of the massive lust that we share. Therefore, these are one-and-done meetings. (Just in case you're judging me right now, I only play it safe and I don't do anal penetration... if it helps at all.)

Almost a month ago, I met up with a dad (divorced with a kid), who is almost twice my age. I am in my mid-20's and he is in his late 40's. We hit it off well, and I ended up spending the night, which I had never done prior to that night. We held each other as we slept. When we woke up in the morning, we made out and held each other again before I left.

Due to busy schedules, we were not able to meet each other again until a week ago. This was the first time ever that I met up with a guy for a second time. Due to scheduling constraints, I couldn't spend the night. But we did everything except actual sex, after which we just lay beside each other and talked for almost an hour.

During the conversation, he mentioned a couple of times how he's old enough to be my dad, and that he's very concerned about our age difference. He also talked about how I'm a young and attractive guy and that I can probably get any guy I want. I told him that I wouldn't have come back if I wasn't interested, but I don't think that convinced him that I really felt that way. The weird thing is... he's never really been in a relationship after his divorce, and I really am not looking for a relationship either because I'm not out. And so, the fact that we were even talking about the age difference was pretty strange.

We were supposed to meet up again a couple nights ago, but something came up. Although I was looking forward to it, I was cool with it because there are some things that are out of your control. However, somehow I kind of feel like he's avoiding me because his cancellation message was pretty cold. There was no mention of him looking forward to the third "date" or that we should see each other again soon. I sent him a message back after he cancelled, but he hasn't responded to a message, which although it doesn't have a question, is something every other person would reply to. Normally, he is pretty quick to send a message back, but I have not heard from him at all.

I don't want to send him another message because I don't want to be overbearing. But I want to know if there is anything up. Should I send him a message anyway? Or am I just being paranoid and reading too much into it? And what is the significance of him talking about the age gap?

 

[saymyname]

Dude. This guy is divorced, and twice your age, and you're in the closet. This is a recipe for disaster.

Don't send him another message. If he is still interested, he'll explain himself. It's very possible that the age gap freaked him out.

In the mean time, have you thought about coming out and meeting someone relatively your own age, with less baggage?

 

[wappyboy]

I don't really think I'll be coming out anytime soon... and I haven't really met anybody interesting enough closer to my age. Actually, I don't usually get attracted to anybody my age so that makes it a lot tougher for me to find anybody my age.

Why would he get freaked out if we've only been with each other twice, and we first met under the pretense of just having no strings attached relations? I know the chemistry is there though so I guess that sort of invalidates the NSA part.

As far as being in a relationship, I'm really not looking, but I'm not opposed to being in one either. It's more of a day-by-day kind of thing for me... be open to getting to know somebody and see where it goes.

 

[wappyboy]

If you're not truly looking for a relationship and you're just fuck buds, I'd suggest you not worry or think too much about it.

From the sounds of it though, you both have some sorting out to do. Do what you feel comfortable with...if I were you, I'd just take things as they come, don't get wound up about what's "appropriate"--be it your text responses or other modes of communication.

Only ever be honest (to yourself and others), never fear that honesty will ruin something like a relationship. If it did, you never had whatever it is you had to begin with.

I wasn't looking, and I thought we were only going to be FWB's, but I suppose that conversation kind of complicated things. We both know that there is connection there, but we don't necessarily want to be attached either. That's why it's a bit confusing at this point. Do you think maybe we should have a talk to set/take down boundaries?

I guess you're right. We also talked about honesty and just being as straightforward as possible. I'll probably just give him a week or two. If I still don't hear from him, I'll try one more time to reach out to him. At the very least, I just want an explanation IF something is bothering him. Then again, I might just be overthinking it... so giving him time to get back to me could be the smart thing to do as well, so as not to ruffle any feathers.

 

[wappyboy]

Thanks. If I still don't hear from him within the next week, I will try and set something up so we can talk.

Thanks also for that last statement. I know sometimes people here try and be nice and say something to encourage those who are asking for advice. I think it's better to hear the cold, hard truth so I could have a reality check.

 

[Treborf]

You're way more invested in a Craigslist hookup than you should be. There's nothing wrong with them, but these sort of things are always going to be fleeting. Save the sober discussions and motive-interpreting for actual relationships. Just enjoy this guy when he's around and when he's acting weird and distant, then on to the next one. But to answer your question, send him another message if you're into him. But try to quell your expectations.

 

[8tomtoms8]

Hey Wappyboy,
I think you've seen about all you'll see of him. You're young, innocent, and your heart is wide open. He is none of those things. How much can you really have in common??? It is a big ego boost for him that he can still attract a guy who is 20 ( I can say that since I am 44 myself) but he isn't going to be able to really continue anything with you. You two are at totally different places in life. And honestly, he'll be much happier with a guy near his own age. You may be a great fellow, but you can't make up for 25 years.

As somebody already mentioned, look for a guy around your age. That way if you are lucky enough to find a connection with someone, you can both experience life's journey at the same time.

Best Wishes.

 

[wappyboy]

You're way more invested in a Craigslist hookup than you should be. There's nothing wrong with them, but these sort of things are always going to be fleeting. Save the sober discussions and motive-interpreting for actual relationships. Just enjoy this guy when he's around and when he's acting weird and distant, then on to the next one. But to answer your question, send him another message if you're into him. But try to quell your expectations.

I agree. Craigslist hookups should only be for no strings attached encounters. And I still feel that way. I guess what I'm trying to get at is that this guy is one of the sanest ones I've met, and that we could actually have a long-term physical relationship. But with the complications, I don't know how much longer this setup is going to last.

As far as being into him, I don't think being with him twice is enough to gauge if emotions can be added into the mix just yet. Like I said, I am not looking, but I am not opposed to having that either.

 

[wappyboy]

Hey Wappyboy,
I think you've seen about all you'll see of him. You're young, innocent, and your heart is wide open. He is none of those things. How much can you really have in common??? It is a big ego boost for him that he can still attract a guy who is 20 ( I can say that since I am 44 myself) but he isn't going to be able to really continue anything with you. You two are at totally different places in life. And honestly, he'll be much happier with a guy near his own age. You may be a great fellow, but you can't make up for 25 years.

As somebody already mentioned, look for a guy around your age. That way if you are lucky enough to find a connection with someone, you can both experience life's journey at the same time.

Best Wishes.

So true. As of right now, the only things we have in common are our seemingly insatiable desire for physical intimacy, our singlehood and the city where we live. Regarding the ego boost, if anything, I think it's bringing out his insecurities more than anything. After all, he kept on questioning the massive age gap and my attraction to him in such a tentative manner.

I think the age gap only matters when you are in completely different stages in your lives. But as far as maturity is concerned, a guy in his mid-20's can be as mature as a guy in his late 40's. Of course, there aren't too many guys in their mid-20's who are mature, but I'd like to think of myself as one of the rare ones (way to pat myself on the back there. Haha.). But you are right with the experiencing life's journey at the same time issue. Considering they say the same thing about choosing your doctor, it probably works the same for a life partner. )

To be honest, if I were to look for somebody my age, it would be a woman. I'm still attracted to women, and I would like to have a family someday. I guess right now I'm just being experimental.

Thanks for your time.