Am I being too picky or am I missing something?

About 12 years ago I worked for a small company where I was the only female employee. Three men worked under me, all friendly enough, but one was always flirty. I was in a relationship at the time. I suppose i was flirty ( more playful than flirty) back but my then partner had seen us interact on multiple occasions and was never threatened or bothered by it, nor did she have any reason to be.

This individual had a car accident and came to my house that I shared with my partner, randomly in the middle of the night. He only knew where I lived because he drove me home from work once. I still to this day don't know why he came and he has no answer when I ask him.

He didn't return to work after the accident and I soon after found other employment and we lost touch. A few years later I ran into him and his then girlfriend at the grocery store a few times. He added me on facebook. We chatted occasionally, nothing more.

A few years later my partner and I had split, he was single and we started talking again. He would constantly ask me to do things with him, come hang out etc and I always said no. Eventually he got tired of asking and we stopped talking.

A little time passed and I was at a bar ( which is something I never do, it was the most random thing) and the people I was with said they had some friends coming to join us, low and behold he was one of them.

We started talking on facebook again, he continuously asked me to hang out, told me he liked me and has often thought about me over the years etc. I said no everytime.

So fast forward to about a month, month and a half ago he starts talking to me online and through text. Same thing, hes constantly asking me to do things and I consistently say no. The other night I finally agreed to hang out with him and we took my dog for an hour long walk.

My mother knows him ( not extremely well ) but she knows him and she constantly questions why I won't just give him a chance.

The other morning I woke up and realized I was suppose to start work early that day and was going to be late. He asked if I wanted him to drive me and I thanked him for offering but told him no.

I quickly got ready and when i walked outside my house he was there waiting to drive me anyways.

The people I converse with at work were in awe of his gesture and said I need to give him a chance.

Here's the issues:

I don't feel like I'm attracted to him at all and I don't feel any sort of spark.

It sounds mean to say, but our intelligence levels are definitely on different levels. Most times I feel like I am talking to a child.

I like deep personal intense conversation, where he likes small chat.

We have a very different thought process.

I get annoyed with him quite easily and I'm not afraid to tell him that.

He smokes which is a big turn off.

On the other hand, he is caring and generous and always tries to be helpful in some way and always tries to make me laugh.

And heres the biggest thing I think for me is he hasn't worked since his accident about 10 years ago. He lives off the settlement money he won and money from his insurance / disability. However, he is constantly going to sporting events, crossing the boarder to go shopping, renovating his house, going to the casino etc etc.

It is extremely frustrating for me to know that I have to get up and bust my butt every day and still struggle financially, yet he's at home on his butt or doing fun things I personally don't feel like he's earned. He's currently trying to plan a trip to California and I'm completely mind blown that he thinks thats okay.

I haven't dated anyone in over three ish years. Am I just looking for reasons not to get involved? Am I missing something?

I have really bad anxiety which is my main reason for not hanging out with him, I don't really hang out with anyone. I also don't want to hang out with him and give him any false ideas even though I've been clear about my intentions.

To be honest, he sounds creepy. You don't need to list all the negatives, (although they certainly add to the number of reasons not to date him). If you did date him, I don't think you would be able to get rid of him. He's too needy and clingy. Your mom just feels sorry for him. That's not a reason to give him a try. You're not being too picky. He's just not compatible with you.

He's definitely not bf material for many of the dealbreakers you listed (no spark, etc.) And it doesn't even sound like he's compatible with you as a friend. It's good to have standards because you only have one life to live on this planet. The fact you haven't been in a relationship for so long is because you've isolated yourself with your anxiety and you haven't put in any effort to find a new bf, because although for some people, a great partner will walk into their lives, but for many of us, we have to date a boatload of men to find the one rare one who meets all of our main needs, and that means joining in activities where single men your age congregate: Meeup.com, co-ed sports team, dance lessons, volunteer work.

I imagine you should consider getting treatment for your anxiety for your own well-being, and also so that when you do get a bf, you won't make him the sole center of your social life. Establish a support system of at least a few girlfriends to hang out with, maybe by joining others in hobbies/interests you can be passionate about. Take care.

I haven't dated anyone in over three ish years. Am I just looking for reasons not to get involved? Am I missing something?

Yes, you're missing the fact that it's your love life, so nobody else gets a vote.

Stop telling people about the guy, and they'll stop encouraging you to pursue a path you don't want. The people who love or like you and know you haven't dated in years will perk up to any mention of a guy on the scene because they want you to be happy. So stop leading them down the wrong road, and they'll stop trying to drag you there along with them.

Most people are NOT our match. That's just natural odds. The fact that you don't pursue dating using apps or meetup.org or other means is your own business, but it makes no sense to highlight stories of the behaviors of a guy you're not interested in to people who are hopeful you will pursue dating.

You've spent enough time with the guy to learn whether you're attracted or not. That IS giving him a chance, and you have your answer. So skip him, and zip the lip. When you want encouragement from people about someone or something that feels 'right' for you, that's when to raise the topic.

I agree with the other posters but I'm also just wondering why you keep constantly interacting with this guy if you're not into him? I mean, he's made it extremely clear that he wants to date you but you have no interest in him. So why do you keep talking to him on a regular basis? I'm sorry but it sounds to me like maybe you're just lonely and/or want male attention and that you're actually encouraging him, whether you realise it or not. This guy is clearly not just looking for friendship, nor does he respect your boundaries. If I was you I'd just delete him from Facebook and cut him off.