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There is a man I have known and had a crush on for about 10 years. We seem to go out once every 5 years or so. We're Facebook friends, have mutual friends, and he works with my cousin. Whenever I am single I get matched with him on online dating sites. I've just been through a horrible breakup with a man I thought I was going to marry. I broke up more than two months ago and have tried to get back out there even if just to distract myself, but have not found anyone who seems worth going out with. I've gone out with two seemingly eligible men and have had no chemistry with either. Last week I had dinner with my ex and his coldness broke my heart, but gave me some closure.

 

I decided to get brave and text the guy I already know. We texted a bit just catching up (he thought I was still living out-of-state) and then I suggested we get together and catch-up. We set a date and location to grab wine over the weekend. We didn't talk most of the week, but he texted the day of to confirm and set a time. We met up and spent 3+ hours laughing and flirting. We talked about some future things we should do together. During that time he said that he considers himself an introvert by nature and tends to only go out when others invite him. In all of the time I have known him, I have never been aware of a girlfriend. When we hugged goodbye I kissed his cheek and he said something about staying in touch and I responded that we should try to see each other sooner than 5 years. I texted this afternoon and said it was nice to see him last night. He responded, "Ya you too!" It's nice to be thinking of someone other than my ex, but I don't know if this guy has any interest in me. I don't know if I should pursue things. I would just sit back and see what he does, but I feel like he has told me he is an introvert and in 10+ years he doesn't seem to have ever had a significant relationship. I don't want to scare him and I don't plan on harassing him, but I just can't get a read on things.

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Well, if he never asks anyone out, then that would explain why he doesn't have a girlfriend or had a relationship. I don't know. He might be shy. Try asking him out to a play or a concert and keep it up once a week or once every two weeks and see what happens. Maybe you can open him up.

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Well, if he never asks anyone out, then that would explain why he doesn't have a girlfriend or had a relationship. I don't know. He might be shy. Try asking him out to a play or a concert and keep it up once a week or once every two weeks and see what happens. Maybe you can open him up.

 

I don't want to seem too desperate, but I really do like him and I fear he might just be awkward at dating. Then again... he could just not like me. We spoke about going ice skating so maybe I'll wait a week or two and then see if he's up for it.

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He doesn't sound overly interested, based on what you wrote.

 

This reads more like a friend situation, and he's happy to catch up, but I don't sense that he's looking for a date at this point.

 

You might be entirely right. It was Saturday evening drinks and our conversation was rather flirty. I said I hadn't been to a particular place to skate at Christmas time and he said he would have to take me. We talked about his facial hair; I said I liked it and he said he had planned on getting rid of it, but he would keep it. There was talk of going to an amusement park and he did impressions of being extra manly. We never really established if it was a date or just old friends catching up. We didn't talk about dating sites or any of that, but we spent hours talking about politics and common interests. I never did mention that I had seen him on a dating site, but according to his profile he wants a relationship.

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Does he know you're just coming off a difficult break-up?

 

We didn't talk about relationships at all. We're Facebook friends and if he viewed my profile he would see a ton of photos of me with my ex. The photos of my ex end a couple of months ago and then it is just photos of me with friends, family, work, etc.

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I think it's likely better if you just approach this as a casual arrangement for now. See him when your schedules line up, but don't go out of your way to plan regular dates.

 

I say that only because it's clear from your previous threads that the break-up hit you terribly hard. Trying to ignite a new relationship right now probably isn't going to work well, because you haven't healed yet. I get that it feels nice to have a distraction, but sometimes you need to really work through the emotions in order to truly be ready to move on.

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I think it's likely better if you just approach this as a casual arrangement for now. See him when your schedules line up, but don't go out of your way to plan regular dates.

 

I say that only because it's clear from your previous threads that the break-up hit you terribly hard. Trying to ignite a new relationship right now probably isn't going to work well, because you haven't healed yet. I get that it feels nice to have a distraction, but sometimes you need to really work through the emotions in order to truly be ready to move on.

 

I will definitely keep it casual. I haven't rushed to respond to his texts (sometimes taking a day to respond) and just assumed we weren't on for Saturday until I heard from him. There is a good possibility that he has no interest in me and I don't want to make it weird since we know a lot of the same people. I will probably text him at Thanksgiving and go from there. I don't mind initiating things some with an awkward guy, but I don't want to be chasing someone who doesn't have an interest.

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My best friend thinks I should text him today just to keep a flow of communication going... thoughts? I really have an enormous crush on him. He has a lot of the qualities that I valued in my ex. They have the same profession, common friends, and many of the same hobbies.

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