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After 2 1/2 years of not dating Lost went on a date! Here is my story...

lostandhurt

By lostandhurt
in Dating Advice

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lostandhurt Grand Master

lostandhurt

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Well it has been over 2 1/2 years since I have been on a date. I wasn’t actively searching, I basically just didn't try. I contemplated doing online again and did a fare amount of window shopping but never reactivated my account(s) and kind of hoped it would happen naturally like when I was younger. Just meet someone in my daily life and flirt a little and go from there.

 

In these last 2 1/2 years I have had a blast. I am happy, my life is full and there is a large portion of my time spent helping disabled people (children to adults) get into and enjoy adaptive sports. But I always missed that connection with someone special.

 

There is this woman I have known for 10 plus years that I always thought the world of and considered her beautiful inside and out. She went from being a professional that saw my son to a friend over the years and we always kept in touch as our worlds in the disabled community crossed paths frequently. Well she got a divorce 2 years ago and being Lostandhurt I offered advice but kept a respectful distance. I found myself talking about her to friends and family more than I usually talk about people in my life until one day my nephew said to me “Just ask her out already” I gave a few lame excuses why I shouldn’t and he called me out on them and threw some of my own advice I had given him back at me. That set me down a path of going back and forth if I should ask her out. Being friends all these years I never thought of her “that way” until now and finally took my own advice that I give here frequently which is to be brave and call her! (Full disclosure it took me 3 or 4 days to actually get up the nerve to call and I sat with my phone in front of me for maybe 10 minutes before I finally called her) I did and after a few missed connections finally talked on the phone and caught up. Then came the time to pull the trigger. If you ever met me in real life I don’t think you would describe me as shy so I just said “The reason I called was to ask you out on a date” then there was silence….. The first word out of her mouth was “Seriously?” I said yes seriously not knowing if it was “you have got to be kidding me, you are actually asking me out because I am not interested in the least” or “I am pleasantly taken by surprise and don’t know what to say” It turned out to be the latter and we talked a bit longer and she told me she had started dating a little but it hadn’t gone too well but she needed a little time to wrap her mind around the guy she has known ten years asking her out.

 

Well I got a call from her a few days later and in all honesty I expected the “I don’t want to risk ruining our friendship” line as she turned me down. She was concerned about that but said she would love to go out with me.

 

The date went very well and we talked for over 2 hours and I didn’t screw up or make any big mistakes but I have to admit I am out of my comfort zone here. I usually do pretty well on dates but I have never dated someone I have known as a friend so the things I would usually do or say just don’t feel right. I may be over thinking this or I may not be, I don’t know.

 

We hugged in the parking lot after the date (standard for me on a first date) and went our separate ways. She texted me before I got home thanking me for dinner and the lovely evening. I responded that I did too and I am looking forward to when we can get together again. I got an enthusiastic “Definitely”

I am sure I am in my own head too much on this and should just play it by ear but now I am thinking “when do I try and kiss her” “is it too soon to invite her over to shoot pool and have dinner” “what should the next date be” I guess this is normal for most people dating but I usually don’t over think these things and it all comes naturally to me. Not this time…

 

So that is my story. You can date without OLD or clubs and it can be enjoyable.

Wish me luck and if you have advice I am happy to hear it.

 

Lost

WithLove Grand Master

WithLove

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I'm super excited for you!! I think that the answers to your questions will come naturally in time. You know each other pretty well already, so don't be surprised for "deeper" topics to start surfacing sooner than usual.

 

Just be yourself... and... try really hard not to try and offer council on stuff you do here!!

tiredofvampires Proficient

tiredofvampires

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Hey Lost, good for you! Congrats on taking the plunge and confronting your fears. As I always have said...I've always found that when you are friends first (and the longer history, the better, so you're in a good spot), it can pave the way for a more solid footing. You know a lot about each other already, so it's like taking it to another level.

 

Trust yourself to do what's right in the moment, as it arises. Some things you can't plan even if you wanted to.

 

Hope this is the start of something really good for you.

NightLily Collaborator

NightLily

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This post is so adorable! Oh wow, this really made my day ...

 

 

 

My personal suggestion, have the next date be something fun. Something you can both get a little excited about. Looking forward to seeing updates!

catcountry Collaborator

catcountry

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You gave me some food for thought almost 2 years ago that turned my life around. I wish you the world. Take it slow and may you be blessed with a wonderful relationship.

lostandhurt Grand Master

lostandhurt

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Thanks to all of you for the supportive well wishes. Due to schedules there isn't an opportunity to see her again for a week.

 

I was thinking something fun as well. Not sure yet but I am sure something will come to me. I got so used to the online dating routine and how that usually goes I want to wind back the clock a little and approach this differently. I am in no rush and this is definitely a want not a need for my life.

 

I like the way this feels...

 

Lost

PICCOLLO Enthusiast

PICCOLLO

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Nice job!

 

Sounds like its all going well so far. I hope you're enjoying things and not overthinking it too much.

 

If you listen to your own advice you'll do fine. Easier said than done when its all happening to you. 😜

IAmFCA Grand Master

IAmFCA

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Love love love this post. A few reasons, chief among them, Lost, you have shared with us a vignette of human triumph. Resilience is the beauty of the human experience, and we lose faith in our ability to rise. You've just illustrated it.

 

So many other little facets.

 

- How happy you are, on your own. Perfectly captured the happiness and still the desire to have that special connection.

- The value of our friendships, and friendship as a foundation for a romantic (need a better word) relationship. This, IMO, is the challenge of OLD in particular, that the time line is Now or Never, with no time available to get to know one another first.

- How easy dating is when it is just dating. How it becomes more challenging when we hope to achieve a goal with it. How you detached from that goal at least a bit in order to take the risk of initiating, and surviving her moments of reflection. How it is hard for the extroverts,for whom gab seems to come easy.

- How now you have the same questions we all do - when, how, what next, even knowing her for 10 years.

 

Have faith in who you are and who she is; you will be able to sort it as it unfolds.

 

Fun!

lostandhurt Grand Master

lostandhurt

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Dude, this is awesome! And you didn't text her. You CALLED HER and ASKED THE WOMAN OUT. So many young men and women can learn from you.

 

I certainly couldn't tell every guy here to call and not do it myself. In fact I left her a message, she called back but I missed the call, then I called back and she missed the call so it was kind of a strung out thing for a few days. I did think it would be easier to just text her but I didn't because it was an important conversation.

While we were talking after I had asked her I told her I didn't want to text you to ask and she told me she was glad I had called and that she appreciated it.

 

Allowing fear to control my life is not something I want to do.

 

Lost

SoulTaker Collaborator

SoulTaker

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I am sure I am in my own head too much on this and should just play it by ear but now I am thinking “when do I try and kiss her” “is it too soon to invite her over to shoot pool and have dinner” “what should the next date be” I guess this is normal for most people dating but I usually don’t over think these things and it all comes naturally to me. Not this time…

 

Good job Lost. In answer to your questions, I wouldn't change a thing, just because she's a friend. Keep courting her. Don't assume you can shortcut the dating process because you know her. For the next couple of dates, find fun things to do (movies, walk in the park,....). Save the "going to my house" for later.

 

As for the kissing part, everybody has their own view. For me, I've found that women will have their own way of letting you know when that time comes.

nutbrownhare Veteran

nutbrownhare

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Well done you! Just, well done! There are some huge plus points in your favour here:

 

- you're happy on your own

- you're looking for intimacy, which is a perfectly reasonable thing to be looking for in a relationship - and realistic, with the right person

- you're not looking for someone to "complete" you, or any of the other crazy, unrealistic things some people seek in relationships

- you're already very fond of each other

 

However, speaking as someone in their fifties who's now been in a relationship for slightly over a year, after 3.5 years of effectively being single... no matter how experienced we are with all this stuff - marriage, divorce, all that - when we first meet someone new it's like being a teenager again.

 

A teenager with all the angst, elation, excitement and daft thinking we had at 15. Just thought you ought to know!

 

And enjoy!!!!!

lostandhurt Grand Master

lostandhurt

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  • Author
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Well done you! Just, well done! There are some huge plus points in your favour here:

 

- you're happy on your own

- you're looking for intimacy, which is a perfectly reasonable thing to be looking for in a relationship - and realistic, with the right person

- you're not looking for someone to "complete" you, or any of the other crazy, unrealistic things some people seek in relationships

- you're already very fond of each other

 

However, speaking as someone in their fifties who's now been in a relationship for slightly over a year, after 3.5 years of effectively being single... no matter how experienced we are with all this stuff - marriage, divorce, all that - when we first meet someone new it's like being a teenager again.

 

A teenager with all the angst, elation, excitement and daft thinking we had at 15. Just thought you ought to know!

 

And enjoy!!!!!

 

I am usually a very sure minded person and rarely hesitate but this is different. It is kind of fun being out of my comfort zone. If nothing comes out of this I am still all good so either way I win.

 

Lost

lostandhurt Grand Master

lostandhurt

Posted
  • Author
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Good job Lost. In answer to your questions, I wouldn't change a thing, just because she's a friend. Keep courting her. Don't assume you can shortcut the dating process because you know her. For the next couple of dates, find fun things to do (movies, walk in the park,....). Save the "going to my house" for later.

 

As for the kissing part, everybody has their own view. For me, I've found that women will have their own way of letting you know when that time comes.

 

Actually I will probably move slower than I would normally which has also got me thinking if I move to slow the dates will feel less romantic and more as just two friends hanging out. Like I said this is totally new territory for me. I am sure I will do fine as I am pretty good at reading people.

 

thanks

Lost

reinventmyself Grand Master

reinventmyself

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I am sure I am in my own head too much on this and should just play it by ear but now I am thinking “when do I try and kiss her” “is it too soon to invite her over to shoot pool and have dinner” “what should the next date be” I guess this is normal for most people dating but I usually don’t over think these things and it all comes naturally to me. Not this time…

 

I loved this part. For all the sound advise that you have to offer and now you find yourself on the side. Ha ha.

If you need any tips I know a good place to come to find them.

Enjoy! You deserve it.

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