I'm finally ready a decade later but is it too late?

[goodiefun]

Ten years ago I randomly met a man at a party and had a special connection with him. He was visiting my hometown for a conference, and although I was very attracted to him, I did not bring him home that night (which he wanted) since I did not know him (was he some married guy looking for a fling? ), he lived far away (LDR was out of the question for me at that point in time), and I didnt want a random hookup. He was very persistent the week he was in town for the conference and tried to see me every day. I kept brushing him off since I didn't want to be some conference fling and finally agreed to see him at a group dinner he was attending on the last day of the conference. There was no expectation of sex at that dinner (I had explained I would not be a booty call) as the group had an engagement after dinner so I felt no pressure attending the event.

The dinner went well and I got to know more about him. I learned he was older than I thought (9 years older than me), very successful in his career, that we had a shared hobby, and he was friends with one of my ex boyfriends. His accomplishments (both professional and with the hobby) were really impressive and I immediately felt intimidated and not good enough for him. I was also self conscious about his relationship with my ex, as I didnt want to look [bad] by dating an ex boyfriend's friend. He proceeded to contact me for a few months following the conference and I finally proposed we meet up in another city (one closer to where he lived, but still required him to fly to) when I would be there attending a concert with some friends. We met up after the concert and things were going very well. We went to his hotel room and then things fell apart for me. I immediately felt inadequate and not good enough for him. I became worried about looking [bad] because I had dated his friend. I became overwhelmed and couldn't be intimate with him. I did not tell him what was going on. He simply asked if I didnt feel ready, I agreed, and then he held me in his arms all night while we slept.

He reached out to me a few times soon after I returned home from the trip. I tried to get him to meet me in another city again and it didnt work out. We eventually stopped communicating with each other and life moved on. We text a little once a year (this started a few years ago when I saw something related to his work in the news), but I have always been the one to initiate the texts. And I have always kept things on the more formal side since, while I know he is not married, I never know if he has a girlfriend and dont want to send forward messages to someone who may be in a relationship.

These professional-oriented exchanges go on for years. Since he has never asked me any personal questions, I assume he sees me as a professional contact and he just corresponds with me as a networking thing (my industry is adjacent to his and I have opportunities of interest to him). I sent him a professional-oriented message last year and he replied with a message explaining that he doesn't want me to reach out to him to discuss work-related issues and that he is focused on his personal life. I took this as a message to leave him alone for good and closed the door on anything ever happening with him.

Then things changed. Our hobby might put us in the same city this year and I didn't want him to run into me at the event and think I was some kind of stalker. I reached out to ask if he was going to the event and he was very friendly (not like the dont text me about work message) and said he didnt know yet if he would be attending. I feel hope about the situation with him and want to see him for romantic reasons. I dont have the same feelings of inadequacy I had before and could care less about that ex boyfriend (now married with 3 children).

How do I let him know I want to see him for him? And not for our hobby? A few years ago there was a similar event and he seemed genuinely excited about seeing me there but it was cancelled due to Covid. I have always wondered about him and hoped some how we would see each other again. But now I dont want to hope. I want to make it happen. Thanks!

Edited January 21, 2024 by a LoveShack.org Moderator
offensive term

[Alpacalia]

You're sending mixed signals. You say you don't want to be a booty call, yet it took no more than a quick dinner to convince you to go to his room. And then you didn't want to get intimate with him that night.

For whatever reason you weren't connecting with him like you would have wanted to. That's totally fine and all, it happens sometimes. But what exactly do you want with him now? You keep mentioning how you don't want to be the booty call but have you considered he's not interested in that relationship anymore?

You say you texted him for work and he politely told you he's not interested in discussing work, he's focused on his personal life. So don't relentlessly text him, that's all he was saying.

If you want to see him again, just be honest and let him know you would like to catch up and see if there is still a connection or potential for something more between the two of you. Don't mention the hobby or any work-related things, just focus on your personal interest in seeing him again. Maybe suggest meeting up for a casual dinner or drinks, and see where things go from there. But be prepared for the possibility that he may not be interested in pursuing anything romantic with you anymore, and be okay with that.

Edited January 21, 2024 by Alpacalia

[Sony12]

Well just ask him if he would like to go to dinner sometime and see how things go from there and if you two still get along as well in person as you once did. Don't get your hopes up too much though as it has been a decade since you two have seen one another.

If he doesn't seem interested in dating just look for someone new.

 

 

[goodiefun]

We both still live in different cities (but not the same ones we lived in 10 years ago), which is why I cant suggest a casual coffee, drink, or whatever. I need to fly to see him or fly to an event where he might be for our hobby.

It also wouldnt be a booty call now (and would not have felt like one that night for me after the concert) as there were discussions after that initial meeting the week of the concert.

[Foxhall]

1 hour ago, goodiefun said:

How do I let him know I want to see him for him? And not for our hobby?

I enjoyed your story- it is quite close to my heart,

I think your  chances are similar enough to my own- 50/50,(trying to rekindle a ten year old romance)

In your favour, guys typically will always have that attraction for a lady a few years younger,

he indicated he wants to speak with you about his personal life so maybe he's trying to open the door there although I accept the the other interpretation also,

you've really got to nail down this meet but in a casual way and then you can be happy you gave it a chance,

perhaps the dinner option- that at least personalises it and if hes interested he will agree.

 

 

 

[goodiefun]

Agreed. The meeting has to be casual and not a crazy pressure situation for either person. I have not seen him in person in a decade -- I may not have physical attraction for him either at this point. I just want to see him and see how I (and we) feel.

[goodiefun]

But how can you make something feel "casual" when there is distance involved? I could go to his hometown some weekend and hope, by chance, he is there and availability and interested in seeing me but that's a lot of ifs.

[Wiseman2]

41 minutes ago, goodiefun said:

. I have not seen him in person in a decade 

How often do you stay in touch? Are you on social media? Is he single? 

It seems like you would like to make it seem  casual but with the distance that's not really practical. 

All you can do is talk to him about visiting him. 

[goodiefun]

We chat for a little bit twice a year. Sometimes a little more than that if there is something special happening with our hobby or work.

I do not have social media but he has Instagram. He is in his mid-40s and posts maybe once a month. The posts are usually with his sister or his parents (like holiday photos). There is no wife in the photos, so I assume he's still unmarried.

[Wiseman2]

50 minutes ago, goodiefun said:

 I could go to his hometown some weekend and hope, by chance, he is there and availability and interested in seeing me but that's a lot of ifs.

Please just talk to him about visiting. Don't just show up. 

[basil67]

2 hours ago, goodiefun said:

Our hobby might put us in the same city this year and I didn't want him to run into me at the event and think I was some kind of stalker. I reached out to ask if he was going to the event and he was very friendly (not like the dont text me about work message) and said he didnt know yet if he would be attending. I feel hope about the situation with him and want to see him for romantic reasons.

If he was keen to see you, I reckon he would have jumped at the chance to see you at the event.  "Yeah, I'm probably going to that too - we should meet up!"   But he didn't.  

Likewise, when he told you to stop messaging him about business, he didn't suggest that he'd like to get to know you on a more personal level

I think he's not interested and I'd leave the ball in his court

Edited January 21, 2024 by basil67

[goodiefun]

The event is being held in another country this year, so it's not expected that he would necessarily attend. I also did not say, "I am attending X this year," because I didn't know if I was going to go. I have since booked my flight and hotel for the event but have not told him.

[basil67]

5 minutes ago, goodiefun said:

The event is being held in another country this year, so it's not expected that he would necessarily attend. I also did not say, "I am attending X this year," because I didn't know if I was going to go. I have since booked my flight and hotel for the event but have not told him.

In this case, if he was keen he could have said "let me know if you're going - I'll see if I can make it".  Also, the fact remains that when he told you to stop messaging about work, he didn't try and move to more personal conversation.   All in all, I'm not seeing any interest on his part.   Perhaps he's not even single

And all that aside, the two of you don't even live in the same city so maybe it's not personal.  Perhaps he's just not interested in dating someone who is difficult to see. For those of us who value quality time, long distance can be a very unattractive situation

[Wiseman2]

27 minutes ago, goodiefun said:

. I also did not say, "I am attending X this year,"  I have since booked my flight and hotel for the event but have not told him.

Why not? It seems strange that you have this scenario mapped out but haven't even communicated something as simple as that your attending this event. 

[goodiefun]

I haven't mentioned it yet since I'm not sure I should say something. I don't think it's realistic for him to go out of his way to attend an expensive event just because I'm going to it. I rejected him ten years ago, so it would be very strange for him to go just because I am going. I also think it would have been weird for me to prioritize going because he may be going, so I decided to book my travel before I would know his final decision on attending. I am going to the event for me, not him. And he should go for himself, and not me, too. I will may let him know a week before the event that I am attending, so he will know I am there if he has made the decision on his own to go to the event for himself.

But the event isn't really the issue. The issue is that I am tired of being really unclear about my interest in him. Instead of being an adult and explaining that I am interested in him as a person, I have discussed work and hobbies for years. When he said he didnt want to talk about work anymore, I didn't follow up with a personal question. I just ceased communication for a year instead. Why would he think I care about him as a person when he told me his priority was personal stuff and then my response was to disappear?

[basil67]

Still though, you've made an effort to approach him.  If he had any interest in keeping things going, he wouldn't have dropped the ball.   Yes, it could be that the event is too far, but he didn't offer an alternative.   And besides, he's in another city anyway.   

In answer to your question: yes, you're 10 years too late.

[ShyViolet]

It sounds like he lost interest in you a long time ago and probably wouldn't feel that this would be worth the trouble.  The fact that for the last few years you have always been the one to initiate the texts, and he has asked you to stop, should tell you that he hasn't been interested for a long time.  And the fact that he doesn't even live in the same city as you, I don't know what exactly you think can come of this.

3 hours ago, goodiefun said:

But how can you make something feel "casual" when there is distance involved? I could go to his hometown some weekend and hope, by chance, he is there and availability and interested in seeing me but that's a lot of ifs.

You said earlier that you wouldn't want to appear "stalker-y" but then you say this.  This is a bit stalker-y, honestly.

3 hours ago, goodiefun said:

Agreed. The meeting has to be casual and not a crazy pressure situation for either person. 

He lives in a different city from you, and meeting with you would involve getting on a plane.  There is literally no way for that to be "casual".  I'm not sure what exactly you want from this guy, and I don't think you're being realistic.

[MsJayne]

So, basically you want to cross paths with this guy again but you don't want him to know you want that. You've casually mentioned that you might be going to a mutual interest event and he made no commitment as to whether he would be there or not. I would look at it like this, you've booked your attendance at the event and he knows you're going to be there, so if he shows up and you see each other I'd say you might be in with a chance, but if he doesn't show up you know he's moved on from that stage of his life and isn't interested. When he mentioned that he was focused on his personal life I think he was inviting you to ask him about it, and you immediately dropped the ball. 

[ExpatInItaly]

I wouldn't bother with this. 

It's been a decade, you don't really know each other, he lives a plane-ride away, and he hasn't initiated communication in a long time. I don't see any interest on his end, honestly. 

What is the reason you're still pinning your hopes on a such a long shot? Aren't there any men in your area that would present much more practical dating prospects? 

[ExpatInItaly]

3 hours ago, goodiefun said:

I am interested in him as a person

How do you even know this when you haven't spent any time together in 10 years? 

It appears you have an idea in your head of who he is, but you actually know very little about him. For all you know, he's been married and divorced and ran off with the hot, young nanny. 

Maybe he's great, or maybe he's a total tool. My point is that you are hanging on to a decade-old idea of him, without having a real clue about who he is today and what he's been doing the last ten years. 

[Foxhall]

7 hours ago, goodiefun said:

The posts are usually with his sister or his parents (like holiday photos). There is no wife in the photos, so I assume he's still unmarried.

I suspect this is also true.

calling a spade a spade- you have been flakey on him before and hes likely got his guard up - he doesnt want to get hurt again and maybe feels by keeping you at a distance well at least that keeps away the risk of further anguish,

chances are any of his network he is confiding in are saying the same things as the good people here,  and the problem with that is it puts barriers up and makes things more difficult.

Id revise a little what I said in the previous post about keeping it casual- I think you need to give him something meaningful- let him know on a skype or something that you are actually interested in seeing him again - try to build up a bit of rapport in the interim,

that obviously is more difficult for you also- you have to open your heart as such,

but I think that will give you a better chance,

I suspect this guy is disillusioned with relationships and hes not convinced of your true intentions,

you need to give him hope,

Good luck.

[ExpatInItaly]

OP, keep this mind too: He might not be married, but that doesn't mean he is single either. 

I have been in a committed relationship for many years (I have no interest in marriage), and I don't post my partner on my social media profile. His job is high-security and he does not have a social media presence. 

Please don't assume Instagram is any indication of his relationship status. He could well have a wife or girlfriend by now. 

[goodiefun]

Thanks, everyone. I was really just looking more for advice on how to transition the conversation to personal matters so it was clear that my interests in him aren't just professional (like I only care about him in the context of what he does for a living). They aren't necessarily romantic either -- it has been ten years so I dont know if i would want to have a romantic relationship with him now. I just want to see him and see if the attraction is still there.

He may have a serious relationship or not. I am not trying to break up a relationship, which is why I only send formal sounding texts. It seems like a big leap to go from discussing hobbies to asking if he is dating someone especially when I dont know if i want to date him. As for distance, I have a fully remote job and can come and go as I please. So, LDR is not an issue for me now.  I am open to anyone I think is attractive (or was attractive) to me now that I have the time, money, and flexibility to have a relationship.

[Weezy1973]

2 hours ago, goodiefun said:

It seems like a big leap to go from discussing hobbies to asking if he is dating someone especially when I dont know if i want to date him.

I don’t think you have to do this. Like you said, you don’t know whether you’ll still be interested in him or he’ll be interested in you. So first step is either to meet up and since that tricky due to distance, see if you can set up a video chat just to “catch up”. And then go from there. See what happens naturally.

[stillafool]

On 1/20/2024 at 11:02 PM, goodiefun said:

I also did not say, "I am attending X this year," because I didn't know if I was going to go. I have since booked my flight and hotel for the event but have not told him.

Why not?  I'm not really seeing where he's all that interested.  He's had plenty of opportunities to ask to see you and to try show you through conversation that he has a romantic interest but he's not biting.  I think if you want to know how he feels you should stop playing cool and ask to see him and find out how he feels.

Edited January 25, 2024 by stillafool