I've liked this girl I work with for a couple months. I asked for her number a couple weeks ago, and we've texted a few times since. About a week ago I asked her if she wanted to join me for a walk, where I was going to tell her how I feel. She said she had to watch her niece, but then responded with 'next time?', so not all hope was lost.

Today I we were texting some more and I asked her if she was still up for a walk. She said she had just gone for one, but then counter-offered that I go with her for a run in the morning.

We get along great at work, and all the signs are there that she likes me, at least I hope that's the case. We make playful physical contact, joke around, make eye contact, smile, all that. But I'm not sure if that means anything. Unless a girl tells me she likes me, I don't have a clue.

I guess what my question is, is what's the best way to proceed? This wouldn't really be a 'date', I just wanted something outside of work where I could tell her how I feel. And I don't wanna see any 'don't date your coworker' comments, because not saying anything and wondering 'what if?' is not an option, and I'm prepared to deal with the potential awkwardness as a result of these actions.

Anyways I was thinking I'd meet up with her, run and talk for a while, and then at some point just tell her.

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I would recommend against just flat out telling her "I like you" or anything along those lines. That screams awkwardness. Based on what you've told us here, she's into you. Good. Now capitalize on it. Take her up on her offer to run together.

After that, I suggest asking her out on a date (a real date) on your terms. Something like dinner after work (on a Friday would probably be best) or a fun date on a weekend. It sounds to me like she'll accept, so that's good. Then from there ask her on a second date. When you two are comfortable enough, talk about going exclusive. But just telling her "I like you" etc, etc is a bad idea in my opinion. 

What D.J. said, in spades.  Telling her how you feel is pressure for her to return those feelings, so if she's ambiguous, shy, or at least not ready to marry you (!), her most likely response is to back away.

Take her out and let her decide how she feels, being with you.

Alright, thanks for the advice. I'll ask her out after and we'll see how things go.

Good luck! Let us know how it goes!

So we didn't end up going for a run yesterday. Her grandmother got sick and she ended up spending the morning in the hospital. I saw her at work today and told her that if she wanted to go for that run to let me know, and she said she'd probably go on Monday. We figured out that we don't live far from each other and figured out a place to meet.

Any suggestions on what to do for a date? Skating is usually what I go for, but seeing how it's July that's not really an option. I was thinking bowling.

First off, it's a good thing she's still down for a run. It means shes interested in doing things with you. 

As for a date, bowling could be fun. I've never been on a bowling date but it sounds good. The only drawback I can see is that it is a sport and that might not go smoothly, especially if she's not good at it. Bowling is just one of those things that if you're not good at it, it sucks to do it. And for all I know (and for all you know) she could really such at bowling. Or she could be really good. But it's probably best to assume, for right now, that she sucks at bowling. 

I would suggest maybe drinks after work on a Friday and perhaps a movie to go with it (even better- a movie theater with a full bar. I know of several in my city). A Saturday lunch date could be fun, wherein you go to a good coffee place and maybe a good used bookstore. I personally love used bookstores and I think it'd be fun to do on a date. Being that it is summer, walks outside are certainly an option. Find a park and take a walk. Good opportunity for talking and getting to know each other. Take a bike ride together somewhere. That could be fun too. Lots of options for summer dates. 

To echo what D.J. said, it is a really good sign she is still up for the run with you!

I would, personally, would make the most of the summer and sunshine. As D.J. suggests go take her to a cafe for lunch then I would suggest to go for a stroll through a park. If you find a nice spot to sit and chat then that would be awesome.

The idea is to just keep building the connection through talking about things that interest you and her. Hopefully it isn't all about work =)

Without having known how much you interact with her at work and over the last few months, I would normally not do a movie date until you are well comfortable with each other.

One idea that popped into my head is that it sounds like you both enjoy being active so maybe even a local hike somewhere with a packed lunch would be good if she is quite the active type.

Richard from Romantic Missions

Alright so I just got back from my run with her. Went pretty well I thought. Towards the end I asked her what her plans for the rest of the week were. She said she was going out either Thursday or Friday and then working on Saturday, so I asked her what she was doing Saturday after work, and she said she might be going out.

When we left she said we should run again sometime, and said she'd give me a hug if we weren't all sweaty. I'm not sure if she's making excuses about Saturday, and she's just trying to be polite, because it's clear that I was trying to ask her out right? I just don't even.

She was telling you that she wants you to ask her out. She has potential plans which means that if something better comes up she will take it.

 

Asking a woman out on a date, is telling her that you like her and want to date her. You don't setup some elaborte thing to tell her that you want to date her, you simply ask her out.


Don't be wishy washy, have a plan. "Saturday there is a blah, blah, blah, you should join me" or even just "Join me" without that should.

 

You were trying to ask her out and you clearly failed at it because you didn't ask her out.

You were trying to ask her out and you clearly failed at it because you didn't ask her out.

This.

First of all, take a deep breath. Stop over thinking this. You successfully went on a run with her. Good job!

Regarding Saturday, I don't think she's making excuses. Because to be honest, you were not being clear enough about your intentions. You'll probably see this in retrospect. I'm sure you were clear in your head- but she can't read your mind. You should have said something like "if you're not doing anything after work on Saturday I'd love to [insert date idea here]" Then you can employ the Brad Pitt rule: if she has an excuse to not get together Saturday *and doesn't offer another time* she's not interested. If she has an excuse but offers another time to get together (as she did with this run), she's interested.

In the future, just be clear about your intentions. Don't beat around the bush to ask her on a date- just spit it out man! Good luck on your future endeavors with this woman.

Lastly, take the hug offer as a good thing but don't read too much into it.

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