You shouldn’t allow yourself to get so emotionally invested so soon
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+1 for coffee. Better to know immedately than to sit around, wonder if he will call or text and obsess, not sleep, etc.
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This is the very reason you naed ro know where you stand upfront. Before you invest too much time and emotion in this venture.
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Coffee.
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As a guy, I’d say I would honestly feel good if a girl asked me out. In my relationship, I’m the typical “guy” or whatever you want to call it - paying for dates, etc. but I wouldn’t have been upset if my girlfriend had made the first move. I am a teenager (19) though, and I don’t know how old you two are, so maybe that changes it.
I’d also go with coffee rather than a drink or something. Like others have said, see if you two can have good conversations and have anything in common. I’m guessing this would go better than if done at a bar. Plenty of relationships have started from meeting in bars, and maybe this guy really is a great person, but don’t try to find your Sunday afternoon person at a Saturday night place!
And if he says no, that’s a real bummer, but at least a relationship never started so it’s not as bad as a breakup.
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Why don’t you let him get your number and propose you something ? tease him, we are not stupid, we know when a girl has a crush for us ! If he is single and want to know you, he will do the move for you
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I should clarify.
I feel like Spock is getting a lot of reasonable advice on all fronts about how this isn’t a big deal and she shouldn’t freak out about it. That’s all fine and dandy, but it IS a big deal to her and she’s going to freak out about it until something is done about it. It’s not going to help her to hear that guys are guys and it’s all in her control - guys have as big of a range of personalities as women do, and she’s hoping she found one who will treat her well, and not like garbage.
My point is, your best chance for success, AND the only way to know if this guy is for real, is to go with the noncommittal, but hey-I-sort-of-like-you coffee invitation.
Don’t numb yourself because this doesn’t seem like a huge deal to people on the internet. After what you’ve been through, maybe this is the biggest thing you’ve experienced in a long time, and I just wanted to acknowledge that.
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Holy shit thank you for saying this.
You are 100 percent right . It is a huge deal to me. It has been years since I’ve had genuine butterflies and this is the first time they’ve been for a seemingly nice guy.
I cannot like your post enough 
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DONT do the first move, i repeat DONT DO THE FIRST MOVE
It’s terribly difficult, but try not to pre-write it. Leave it as a clean slate, and be open to any number of possibilities. I know that sounds like a disaster waiting to happen, but it also leaves open all of the other good possible outcomes.
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I’ve been on a few dates in the last month or so, after being married for forever, and this is what I have learned. It’s okay to go hang out with someone as friends - it doesn’t have to be romantic and shit, it can just be chill.
When I was younger, it was always about the chase and getting into bed. I guess because I am dating women the same age as I, it’s more about being friends.
I would try (emphasis on try because I know how we are) to keep it a friends thing at first, not rush into anything. If you get a no on coffee, he’s just got a lot of friends, no rejection. If it’s a yes, you get a chance to see how fucked up he is while being friendly - no pressure.
FWIW, I’ve been on five dates in the last two months, all of them initiated by the women. They have all been low key with a lot of great conversation and no real physical contact. I don’t know if I’ve been “Friend Zoned” or not, but it’s all cool. I’ve gotten to know these three women better and consider them friends. Win/win.
Either way Spock, you’ll be good. Trust in that.
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@T3hPwnisher already nailed it, but reddit is a sewer and I would not put much stock into anything you read there (or here, for that matter, even though we’re a few floors above the sewer on this forum).
Working the door at a few clubs occasionally, I have women make passes on most shifts. It’s always flattering, even if I have no interest. I think most guys like the ego pump and I think most guys are decent enough not to be dicks about saying no.
Just send your signal in a classy way. A few weeks ago I had an attractive lady who was chatting me up while I was working the door blow any chance she had by hugging me, then moving right to sucking my earlobe and then biting - HARD. Too slutty, too soon, too painful.
Coffee or drinks is straightforward. It doesn’t mean you’re jumping into bed but clearly signals some level of interest. It will give him a chance to test the waters in a neutral setting without a ton of pressure. Pretty basic first date stuff.
Another option would be to chit chat with him a little more at work and find out his interests. Assuming he has a hobby of some kind, feign interest (or not, if genuinely interested) and say how much you’ve always wanted to try whatever his weird hobby is. This leaves the door wide open for him to say something like “Why don’t you come to the Android’s Dungeon on Friday to play Magic: The Gathering?”.
Before you know it you’ll be tapping more than Magic cards!
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Do what you think is best, just be prepared to learn from the experience.
Also, ask him if he does 5/3/1.
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Lots of advice from dudes in here … where’s a chick who has her shit together when you need one?
My best advice I can offer to you @Spock81 is to stop reinforcing this idea that you’re awkward. You’re trapped in a perpetual loop of a self-fulfilling prophecy. You think you’re awkward, you’ve invested yourself into being awkward and you continue to be awkward. If you hear what I’m saying, and try to take action to stop being awkward, understand that it takes time and you’ll still do awkward things.
Reflect on those things you find awkward and how you can not do them again or reduce their occurrence in the future. You have more confidence than you believe, you just have to practice it - reinforce the confident you the same way you’ve seemingly reinforced the awkward you…it’s trial and error. Hope this makes sense.
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You’re thinking too much. Just do something. You’ve got the same problem a lot of men have.
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With a couple of noted exceptions, all my long term relationships were literally arranged by a matchmaker (think of it as analog Match.com), so I have zero advice to give you.
I do wish you well.
As a boss, however, I do cringe at office romance. We have a no-dating-in-your-team or chain-of-command rule, just to keep office drama to the minimum. I suspect you do, too. Maybe crack open the employee manual you were given on the first day and make sure you are screwing up your livelihood (or his).
Assuming you are OK there, asking someone to go have lunch at work (or coffee or whatever) seems pretty logical.
We had one enterprising young man ask for the firm to sponsor small group lunches between young associate teams that don’t necessarily talk to each other (like tax and litigation groups) as a morale boosting activity. We agreed.
Several marriages have resulted from said intra-firm pollination process, with zero office drama.
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@polo77j I’m a chick, whether together or not…
Ok. Imho, you seem to be an emotionally charged gal. To be honest, I’d seek love elsewhere. You don’t wanna “shit where ya eat” if you’re following what i mean.
Ask yourself could you handle it gone wrong? Plus, with the workplace etiquette, it’s not recommended to be blunt due to sexual harassment insanity. I met mr guns in my office complex. When we married we stopped that because it became just too difficult, not on our end, but people fucking suck. It’s like there are no boundaries once you bring your personal life to work on display.
I really wish I could say “go get him” but if things go amiss, do you really want the dude next to you to have a picture of your boobies?
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I guess I should also note in a few weeks I’ll be work from home so I’ll literally never see him anymore
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That would’ve been important. I’ll reassess in a few. Trying to explain gift tax to someone. Geez, they gave their kid 15 k for Xmas, I’m like, wtf, 14 k and not taxed. Geez, it’s not like this number is new.
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Ok, a guys point of view might be better. However, what I’d do, is I’d tell him it’s almost your last day at work and wanted to thank him for trying to help with your glasses by buying him a cup of coffee, your treat. Limited speech and caffeine until you can sleep and or breathe 
before you ask him, remember to breathe as well, you don’t want to be anxiously asking him while breathing heavily.
Baby steps young padawan.
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