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Old 6th August 2017, 7:57 PM   #1
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New to Dating...

I'm really new to dating and I have a situation with a particular woman I used to work with. This is pretty lengthy so you may be able to just jump down to the end. I would first need to probably state that I was once very large, weighing in excess of 470 pounds. I have since slimmed down to 190 pounds but being so big for most of my adult life has caused me to be inexperienced with dating and I'm trying to get started at 32 years old.

This really all starts probably over two years ago. There is a woman that I work with who is very outgoing, friendly, and well liked. She and I would have occasional small talk but again she would talk to anybody so it was really nothing to look into. I started working from home in August of 2015. I had started my weight loss in February of 2015 and it was really up and down. I decided to get my feet wet in online dating and just check it out. I set up an eHarmony account. I didn't pay for it and I didn't upload pictures, I was over 400 pounds of course, and I didn't add any information. I was just browsing around when in November of 2015 I was matched up with this woman at work. It threw me off since I figured someone like her would have a boyfriend but at this time it was merely a pipe dream. Since I had no pictures or info, it's highly unlikely she knew it was me.

Literally maybe a day or two after we were matched up, I was in the office. She was by my desk and made a little small talk. I should also add that our company does some quirky things. We had to come up with a bio in a superhero themes so people can get to know us. I pretty much just copied Family Guy and pretended to be the super devil and my power was a jar of marmalade that makes people commit adultery. Apparently they didn't think that was appropriate so the supervisor edited it and put makes people uncomfortable with awkward silence. I'm known for being quiet but sometimes witty even if I don't think so. Anyways, she read this and said that it doesn't make her uncomfortable. She then started to remark about how plain my desk was since I have no pictures or decorations. She said she was going to draw me a picture to hang at my desk. I was thinking this is small talk and/or empty gesture. At the end of the day as I was leaving, I walked past her desk. I can't even remember what I said but she thought it was funny. As I walked away, I heard her say to a co-worker he's so funny, I like him. Again, I'm over 400 pounds and women just weren't attracted to me so I thought noting of it.

I went back to the office maybe a week or so later and to my surprise was a picture hanging in my cubicle. It looked like it took some serious effort and on the picture she wrote "PS. your awkward silence does not make me uncomfortable." It may have danced in my head that she was interested in me, but I was over 400 pounds so I thought no way.

It turns out she later got the opportunity to work from home as well. We have an instant messenger at work so she would occasionally send me an IM. One time she talked once about a vacation she was going on and would occasionally talk about things like that. She's a friendly, outgoing person so I assumed she talked to a lot of people like that. Fast forward to October of 2016 and our company is having an employee appreciation week. She asked me on IM if I was coming in. I said I planned to on Friday.

Friday comes and I come into the office. Since we both had been working from home, this is the first time we saw each other face to face in nearly a year. This time I was down to 300 pounds and she commented on how good I looked. They changed up the office so we didn't have our old desks anymore so we set up in empty desks. She enthusiastically asked to sit in the empty desk next to her. We talked on and off through the day as much as we could. Mostly small talk. I was still pretty big so I wasn't feeling to confident and didn't think of a relationship.

That following Monday, I'm logged in no more than 20 minutes and she sends an IM. She asked me if I like plays. This got me thinking a little and I said sure. She then asked me if I wanted to go to a play with her and a couple other female co-workers. This is the first time I truly thought this could become a relationship. Of course I said yes. She was trying to get in touch with someone who had tickets since tickets were sold out at that time. In the meantime, she suggested a mystery dinner, again I'm assuming with a couple other female co-workers, but that fell though as tickets were sold out. The tickets for the play also fell through. She said there was a play coming up in February and she would let me know. It may also be worth noting that shortly after this conversation, she shared a post on Facebook that was a video of someone singing I have a crush on you and the title said to share it with someone you have a crush on. She just posted it on her wall, didn't tag me or anything, but she knew I could see it but she also has like 900 Facebook friends so perhaps that was a signal?

Conversation cooled down but in December she messaged me again. There was another co-worker who was leaving the company. This co-worker was having a gathering at a bar after work. Since I work from home, I hadn't seen or talked to this person so I had no intentions of going. She said that was ok and that there were other co-workers who I knew who were going. I agreed to go. I was down to 250 or so pounds at this point and was feeling pretty good. I'm pretty shy and don't go for these things but since she would be there I would go.

I went and she was there. We talked and she said I'm so glad you came. She suggested we should hang out more often and I said that would be good. She then asked me if I was dating anyone. In hindsight this was probably my opportunity. I should have reciprocated and asked her but I didn't. She said she should set me up with one of her friends. I'm wondering if maybe she wanted me to ask her out? There were other co-workers there and I got nervous and didn't do it. We did begin to talk about relationship stuff and if I would do various things like clean snow off a girlfriend's car etc. The gathering finally ended and she reiterated again she was glad I came. It was snowing pretty good that night and the roads were bad. She asked me to send her a message on Facebook when I got home (We had been friends on Facebook since about June 2016). I got home and did and she said once again she was glad I came.

February came and I hadn't spoke to her since that time at the bar in December. I decided to IM her and we had a little small talk but nothing serious. At this point I felt like I blew it and I probably should have pursued her more but I'm so new to this and have no instincts.

Our company set up a bowling outing in March. I normally don't do these things but I knew she would be there so I went. Close to 40 people showed up. I'm terrible in crowds and am not one to mingle and start conversation. She was there and I said hi. Other co-workers who I probably hadn't seen in over a year were there and they remarked on my weight and she said I was looking good but we really didn't have much conversation. I probably came off bad as I'm just not good in large groups. It also probably didn't help that I never really bowled before and was terrible.

I figured I blew my chance and we didn't speak for a long time. Finally in July just a couple weeks ago, she sends an IM and asks how I'm doing and that it has been awhile. I said I was doing well and asked her how she was doing but I was so busy I couldn't get a conversation going.

Last week I go to IM her to kind of try to pick up the conversation again since I was so busy when she IM'd me the last time and I didn't say much but she's not there. I look on the schedule and she has been taken off the schedule. I think she has been let go by the company. My heart sank as I feel like I missed the opportunity. I don't know for certain if she was let go or maybe a leave of absence but she isn't here anymore. I feel like I've broken up with someone I never went out with, but then I remembered she is still on Facebook.

This is where this takes me. I have rarely dated so I'm not sure if she is interested in me? It seems like some of the signals were that she was? I'm thinking now of just doing it and asking her out on Facebook as that is the only method I have of contacting her now. I have a surgery coming up so I'm thinking after that sending her a direct message on Facebook asking her how she's doing and that I haven't seen her at work and is everything ok. So much time has passed if she was interested will she still be interested? I know I probably blew my chance but I feel like I have to at least try and I want to know the best way to do it and if I am correct in my thinking that at one point she was interested?
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Old 6th August 2017, 8:48 PM   #2
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You now have every reason to contact her immediately through Facebook and ask her, Hey, what happened? I see you are not on the schedule." And then hear back from her and then ask if she'll meet you for a drink. It's natural and nice for someone to take someone who either got fired OR got a new job and buy them a drink. She has been very friendly. No way to know, but she certainly gave you some opportunities to get together, so it's now or never.

Take her out as a friend, but then after talking about her situation, tell her you're about ready to start dating and ask her if she'd like to go out sometime.

She sounds nice. Good luck. She is not going to be mean so don't worry about her rejecting you. I think the worst could happen is if she's just already seeing someone.
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Old 6th August 2017, 9:23 PM   #3
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I'm not worried about her being mean. I was thinking of saying something like "How are you? Haven't seen you at work is everything ok?" I don't necessarily want to say I don't see her on the schedule. She works in a different department so I had to snoop to see her schedule. It's public but I have no reason to be looking at it so I don't want to come off as a stalker. I'm just speculating she got fired. This is usually what happens when someone gets let go. It really is surprising since she was a top performer and was well liked by management and co-workers. If she quit the company usually has some sort of send off for people like her who have worked there a long time and are well liked. She's still active on Facebook and there is no indication by her posts anything bad has happened.

She is nice and one of the few women who gave me the time of day when I was bigger. Now that I'm a normal size, I do notice an increase in attention and not just from women. I'm wondering if I'm reading her correct and that at least at some point she was interested in being more than friends? I'm thinking a single woman asking a guy to go with her to a play and a dinner, albeit with other female friends, is a good signal? When we were at the bar in December, she only asked me to message her on Facebook when I got home. Perhaps she already had phone numbers for the other people there? Shortly after she asked me to go to the play, she started posting memes on Facebook about being single almost as if to let me know she's singles. Granted 900 other people would see them to but it happened within days of talking about getting together.
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Old 7th August 2017, 1:41 AM   #4
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First, congrats on losing the weight!

It's hard, but try your best not to read too far into anything you describe. Focus on what you are doing and will do. I think the message you drafted is perfect.

Don't be afraid to fail. Good luck!
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Old 7th August 2017, 2:51 AM   #5
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Also congratulations on losing weight Ok, about your situation. I think your plan is a good one. Two things to keep in mind:

*When you contact her on FB, just don't address "i didn't see you on the schedule" or whatever would make it uncomfortable or like you were going above and beyond to check out her schedule. Sometimes the best thing to do is to take the conversation in the WAY you want it to go. "Hey, how are you, haven't seen or talked to you in a while" is good. No explanation is necessary. I would say you already have enough of a friend basis that you don't need to explain yourself.

And in my personal opinion, taking the conversation away from work-related discussion and showing care or wondering about her in general as a person is good/much better. This new development could be a blessing in disguise. Now that there is (potentially) no work-related reason to get together or see one another, you can develop what is just between you two. And in a one-on-one situation. So much better for you. I think the bowling thing wasn't the best situation for you and maybe you lost momentum with her at that point. (i do think she may very well like you--the only thing that concerned me is when she said she would set you up--but she could have been fishing for your relationship status or to see if you were interested in her). So anyway, just make contact and steer the conversation the way you want it--no explanation needed as to why you are contacting her. "Hey how are you". Of course if she acts weird (i don't think she will) you can always "fall back" on the excuse that you haven't seen her at work things/on work memos/think of a work excuse (come on you can do it, if she doesn't work there, she won't know which is a valid excuse anymore, i.e. some meeting or mass email).

*Second, since you haven't dated much, i would say you are jumping to the end too much and worrying about all sorts of major things and overthinking it a bit when small steps will work with someone you know from real life. People make too much of a deal about friend zone. In your case with her, it's the perfect excuse to start building on your friendship and use those opportunities when you are connecting with her or spending time with her to feel out if there is potential for "more". That's how people who already know each other do it. The dynamic will change. That said, because you don't have much experience and might be a little shy with all of this, you want to make sure you don't play it too timid. You need to take opportunities when you do get them. Say something a little bolder than normal, or where it will make HER wonder if you are flirting with her, and yes do flirt with her. I also think building on it without being in a rush will allow you to be your most comfortable self in this situation.

So if you get a FB response, and she lets you know she is not working there (you should try to get her to say this at some point during back and forth & she probably will for a bunch of reasons) and then say "we should get together" (which you also don't need to over explain nor do you need to know her bf status to ask that question--she will tell you if it's an infringement by saying she can't go bc of her bf or if she directly feels it's a date and she has a bf otherwise it's friendship & networking). Listen, I use this word a lot on the site, saying people should plant seeds. Doesn't matter what her situation is now because all you are doing is planting a seed. Hopefully, you will get to take action on it right away and meet up very soon but if you don't who knows what the future holds & expressing interest in her as a person, above and beyond work, may pay off in the future. A woman I work with sometimes kept running into this guy through work over a period of about 5 years; there was mutual attraction but one or the other or both was always dating someone. Then one day the timing worked out that they bumped into each other again and were both single. They are happily married now. I know lots of stories like this. You have to plant seeds and create opportunities. Take small steps when you already know the person and bigger steps when the opportunities present themselves. In your situation take the big step of reaching out now and small steps within the conversation on FB and if you meet up. Also last note, if you are building toward a romantic thing, you want to use every interaction to EXPAND the conversation to various subjects all over the place. That way you solidify that you are more than work acquaintances and keep expanding at every step of the way. Good luck! And people on here can help as you are going through the process.
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Old 7th August 2017, 7:26 AM   #6
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Definitely reach out. If she was nice to you before now that you are literally half the man you used to be, she probably thinks you are nice & now sexy. Give her a chance. You won't know until you try. You probably thought you couldn't lose all that weight either but you did that. Losing weight & keeping it off is harder then dating. But they are both all about making the effort & being true to yourself.
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Old 7th August 2017, 9:32 AM   #7
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Originally Posted by Versacehottie View Post
Also congratulations on losing weight Ok, about your situation. I think your plan is a good one. Two things to keep in mind:

*When you contact her on FB, just don't address "i didn't see you on the schedule" or whatever would make it uncomfortable or like you were going above and beyond to check out her schedule. Sometimes the best thing to do is to take the conversation in the WAY you want it to go. "Hey, how are you, haven't seen or talked to you in a while" is good. No explanation is necessary. I would say you already have enough of a friend basis that you don't need to explain yourself.
I wanted to show concern especially if she got fired. I am genuinely concerned as I find this perplexing. I checked and she is still in the employee directory. Usually by now they are removed. An email went out and she was part of the email chain. I'm thinking this could be an abrupt leave of absence for some reason, possibly medical? Being out of the office, I'm really not in the loop.

Quote:
And in my personal opinion, taking the conversation away from work-related discussion and showing care or wondering about her in general as a person is good/much better. This new development could be a blessing in disguise. Now that there is (potentially) no work-related reason to get together or see one another, you can develop what is just between you two. And in a one-on-one situation. So much better for you. I think the bowling thing wasn't the best situation for you and maybe you lost momentum with her at that point. (i do think she may very well like you--the only thing that concerned me is when she said she would set you up--but she could have been fishing for your relationship status or to see if you were interested in her). So anyway, just make contact and steer the conversation the way you want it--no explanation needed as to why you are contacting her. "Hey how are you". Of course if she acts weird (i don't think she will) you can always "fall back" on the excuse that you haven't seen her at work things/on work memos/think of a work excuse (come on you can do it, if she doesn't work there, she won't know which is a valid excuse anymore, i.e. some meeting or mass email).
The bowling thing was a bad idea. I tried to back out but the department manager who organized said she was surprised to see me coming and looked forward to it. Since I already RSVP for it, the company spent the money so it would be a dick move. I think at the bar in December she may have been fishing. The first thing she started talking about was am I seeing anyone. She asked about previous relationship, which I embellished a little to make it seem like I do actually date, and then went on about things I would do like pump gas or clean off a car for a girlfriend. I wish I would have asked her if she was single after she asked me and if she said yes, maybe casually reference both of us getting together. That's in the past and nothing I can really do about it now.

Quote:
*Second, since you haven't dated much, i would say you are jumping to the end too much and worrying about all sorts of major things and overthinking it a bit when small steps will work with someone you know from real life. People make too much of a deal about friend zone. In your case with her, it's the perfect excuse to start building on your friendship and use those opportunities when you are connecting with her or spending time with her to feel out if there is potential for "more". That's how people who already know each other do it. The dynamic will change. That said, because you don't have much experience and might be a little shy with all of this, you want to make sure you don't play it too timid. You need to take opportunities when you do get them. Say something a little bolder than normal, or where it will make HER wonder if you are flirting with her, and yes do flirt with her. I also think building on it without being in a rush will allow you to be your most comfortable self in this situation.
I don't even know how to flirt. Even if she becomes just a friend, that probably wouldn't be the worst thing. She has plenty of friends so getting set up with one of them may not be the worst thing.

Quote:
So if you get a FB response, and she lets you know she is not working there (you should try to get her to say this at some point during back and forth & she probably will for a bunch of reasons) and then say "we should get together" (which you also don't need to over explain nor do you need to know her bf status to ask that question--she will tell you if it's an infringement by saying she can't go bc of her bf or if she directly feels it's a date and she has a bf otherwise it's friendship & networking). Listen, I use this word a lot on the site, saying people should plant seeds. Doesn't matter what her situation is now because all you are doing is planting a seed. Hopefully, you will get to take action on it right away and meet up very soon but if you don't who knows what the future holds & expressing interest in her as a person, above and beyond work, may pay off in the future. A woman I work with sometimes kept running into this guy through work over a period of about 5 years; there was mutual attraction but one or the other or both was always dating someone. Then one day the timing worked out that they bumped into each other again and were both single. They are happily married now. I know lots of stories like this. You have to plant seeds and create opportunities. Take small steps when you already know the person and bigger steps when the opportunities present themselves. In your situation take the big step of reaching out now and small steps within the conversation on FB and if you meet up. Also last note, if you are building toward a romantic thing, you want to use every interaction to EXPAND the conversation to various subjects all over the place. That way you solidify that you are more than work acquaintances and keep expanding at every step of the way. Good luck! And people on here can help as you are going through the process.
I'm not a good conversationalist. It kind of helped that we had work as a mutual talking point. I'm not very good at keeping conversations going. Part of the reason I'm attracted to her is her outgoing personality.
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Old 7th August 2017, 9:45 AM   #8
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I'm not a good conversationalist. It kind of helped that we had work as a mutual talking point. I'm not very good at keeping conversations going. Part of the reason I'm attracted to her is her outgoing personality.
Man you were good enough to maintain her interest (even if just as a friend) over the course of years and many pounds! People, especially women, don't just keep talking to people they have no click with. You got this, brother!!!
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Old 7th August 2017, 9:49 AM   #9
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I'm not a good conversationalist. It kind of helped that we had work as a mutual talking point. I'm not very good at keeping conversations going. Part of the reason I'm attracted to her is her outgoing personality.

Extroverts like introverts. We need an "audience." lol

It's not that hard to keep a conversation going. The secret is to ask Qs, listen to the answers then ask a related follow up Q.

You have to willing to answer the Qs that you ask but also don't be afraid of the cliché Qs like "how was your day?"

You can do an internet search for some conversation starters but some great get to know you Qs include:

1. Favorites: movies, songs, meals, etc.

2. Current events -- down play the controversial ones. For example, everybody seems all upset that President Trump called the White House a dump. I can understand that but then I read the NY Times article & was surprised to learn the HVAC hasn't been upgraded since the 1940s; the electrical needs to be overhauled; the roof leaks & they have a fly infestation problem. For a real estate developer who builds new buildings it probably does seem like a dump. You could ask how she'd react to living in a place with those problems.

3. How she got to this point in her life. Why she joined the company where you met? Where did she go to college? What was her major? (Yes that line still works)

4. Childhood memories: best & worst family vacation? sports played? summer camp stories etc.

5. Bucket list things: Where she wants to travel? What she wants to accomplish?

6. Comparisons: cats v dogs; city v country v suburbs; beach v mountains; casual v formal; cruise v ai vacation etc.
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Old 7th August 2017, 11:08 AM   #10
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I wanted to show concern especially if she got fired. I am genuinely concerned as I find this perplexing. I checked and she is still in the employee directory. Usually by now they are removed. An email went out and she was part of the email chain. I'm thinking this could be an abrupt leave of absence for some reason, possibly medical? Being out of the office, I'm really not in the loop.



The bowling thing was a bad idea. I tried to back out but the department manager who organized said she was surprised to see me coming and looked forward to it. Since I already RSVP for it, the company spent the money so it would be a dick move. I think at the bar in December she may have been fishing. The first thing she started talking about was am I seeing anyone. She asked about previous relationship, which I embellished a little to make it seem like I do actually date, and then went on about things I would do like pump gas or clean off a car for a girlfriend. I wish I would have asked her if she was single after she asked me and if she said yes, maybe casually reference both of us getting together. That's in the past and nothing I can really do about it now.



I don't even know how to flirt. Even if she becomes just a friend, that probably wouldn't be the worst thing. She has plenty of friends so getting set up with one of them may not be the worst thing.



I'm not a good conversationalist. It kind of helped that we had work as a mutual talking point. I'm not very good at keeping conversations going. Part of the reason I'm attracted to her is her outgoing personality.
Well you can definitely show concern and should, of course. But if you are worried to look like you stalked her than you just have to pick your poison. Considering that whatever reason might be delicate, I'd let her bring it up OR you can fake that you don't know and say you will see her at the next work thing or see you at work & let her correct you. But if you are not worried to look invasive, it's equally fine to say "hey how are you? I haven't seen you around the office lately (as if you had been in a few times)" and let her fill in the blanks. I think none of it is bad. The level of interest and level of "stalking" necessary whichever way you put it is vague enough or a non-issue. It's only an issue if you make it one or the thought of how you say it makes you uncomfortable. Most important is to approach the situation in a way that gives you confidence and doesn't have you re-thinking things. This one is easier than most because it is FB messaging but you also need to start building your skills so you can take this confidence into phone and in-person conversations with her or other women. Just a thought, can you go to the office to work there for a day to see if you get any intel on what is going on with her? IMO, it's not necessary, would just cause an over thinker to overthink. But if knowing her current work situation would help you then find a way to get that info or try to get it. This is a helpful mindset to get whether you take advantage of it or not on this particular issue. Basically you need to think more multi-dimensional to seize on opportunities. If you spent a lot of time where you're confidence was lower, you may not be comfortable doing this or not have a lot of practice at it. Try not to only think linear or create faux roadblocks. Like you said, "well you don't go into the office so you're not in the loop" as if it was a definitive roadblock. But you could go in or certainly have others you converse with from the office or could just be bold. There are very few "blocks" if you are constantly looking for a way THRU Look for opportunities, advantages, options rather than seeing false blocks. Successful people do & you will need & want this skill.

Ok bowling wasn't the best but it sounds like you may have learned from it. And knowing that you have a tendency freeze up when in an ideal situation presents itself (talking to your crush, going down the dating question line), now you just have to realize that things like this will come along again, either nearly exactly the same or similar enough. Such as being in a similar situation with her again, same line of questioning, what would you do? This is where you would insert some flirting, perhaps ask her to hang out. What would that look like? As with anything, it's best to prepared. As they say, when preparation meets opportunity....Knowing it won't come super natural to you means you need to prepare even more because you will likely also be dealing with nerves. That's one reason why I said take the small steps because as you build your friendship and knowledge of her, things just tend to come up, such as talk of movies, concerts, restaurants, interests, sports and it becomes a much easier leap to hear that she likes this sort of movie or activity and then mention "hey I just saw that xyz is opening next week, we should go together". Even easier if you have similar interests or as she is talking about hers, capitalize on yours where hers and yours overlap. it's not that hard it just needs practice. The nerves will make it hard so it's good to have some ideas in your head though. Keep a list of stuff she is interested in or that you've been meaning to share with her if that helps.

I was going to say, she sounds like a good person to set you up even if it doesn't work out with you two or she is not available. I do think she likes you but that was a little while ago so who knows what the situation is now. It's always good to have friends especially for you, outgoing girls so you can work on your social and flirting game. And expand your social circle.

I'm not saying you can't talk about work. It's obviously the lead in but I would try to get away from talking about it, otherwise it can be confusing as to what you really want from her and/or boring; negative potentially. Well again you have identified a problem: "not a good conversationalist". Why do you say that? How would you address it? I would say putting all the burden of carrying the conversation on an outgoing person is not the answer. It can be a portion of the solution but the entire thing? No bueno. Here's the sneakiest trick to being a good conversationalist: ask questions pertaining to the conversation. That tends to keep it going. Also work on your skills--books, online, real life practice, including on strangers. Just aim for pleasant, interesting and then you can build on that. I have to say that I didn't see that in your posts here--they are engaging enough so maybe carry some of your writing skills out into the real world conversations. Also though I would caution about only letting a conversation (even as you become better at it) become a one way street. It can make you well-liked but not quite as respected or boring if you don't let anyone in on your life, your interests. Once the balance is one-way, it can be hard to switch and people will resist it or you will end up mostly with people who love talking about themselves or thats what they particularly like to do with you. Plus in the end it leaves you empty because if you don't share yourself with others, it's hard to feel close to them--that's going to be particularly important with whoever you want to date, to achieve feeling close will really bond you to them and vice versa.

Keep being positive and send the FB message. Good luck!
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Old 7th August 2017, 9:43 PM   #11
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I'm trying to plan out the conversation. She will likely say she got let go but I don't know how to transition from there.

The more I think about the conversation we had in December, the more I think she wanted me to ask her out. It seems like things really slowed down after that. Maybe she felt I wasn't interested?

I do go in the office Friday. Maybe I can get more information. Not sure it will matter much if only to satisfy my curiosity.
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Old 7th August 2017, 10:13 PM   #12
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Originally Posted by Quagmire243 View Post
I'm trying to plan out the conversation. She will likely say she got let go but I don't know how to transition from there.

The more I think about the conversation we had in December, the more I think she wanted me to ask her out. It seems like things really slowed down after that. Maybe she felt I wasn't interested?

I do go in the office Friday. Maybe I can get more information. Not sure it will matter much if only to satisfy my curiosity.
Well I see no reason to wait until Friday to message her. Why wait? Sometimes the over planning causes more nerves and a bad build up. You have to find a way to lower the stakes of flirting situations/contact with someone you have a crush on so that you can make best of the situation, be your most confident. Don't allow it to hold too much weight--because the truth is at this point it doesn't.

Yeah, your inexperience or insecurities sound like they have been holding you back from expressing yourself or seeing opportunities that are right in front of you, because you believe them to be implausible. The cure for that is more experience, taking risks, putting yourself on the line more than you do. There will be failures and there will be successes. You will learn and you will gain confidence. But you have to try.
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Old 8th August 2017, 2:10 AM   #13
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I do go in the office Friday. Maybe I can get more information. Not sure it will matter much if only to satisfy my curiosity.
Yep, perfectly safe and normal to be a bystander driving past the car crash. You have everything to gain by checking in now and seeing whats up.
You have everything to lose if you dally for another couple months.

Message her. I dare you.
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Old 15th August 2017, 8:46 AM   #14
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So I haven't done it yet. Last Wednesday I was able to confirm she is still employed at the company but everyone was pretty tight lipped on why she's gone. I have to assume now it is for medical reasons and I'm not sure how to approach it. Obviously I want to send a Facebook message but how, or do I even, advance it to asking her out if she has health issues? What if she isn't even healthy enough to go out? I can ask how she is doing and then wait till she gets better to ask her out? Once again health is just speculation but seems the only logical answer if she didn't quit or got fired.
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Old 25th August 2017, 7:56 PM   #15
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So I still haven't done it. She has posted on Facebook about being in and out of the hospital so that is throwing me off. She is off the schedule for the foreseeable future so I would have to imagine it is pretty serious. On top of that, I go in for surgery myself in two weeks. She may not be well enough to go out and I will be having my issues shortly, so what do I do? I'm assuming she's coming back to work at some time. She is still employed there. I'm guessing I can lay down the groundwork and ask how she is doing but how do I, or should I, advance that to a date?
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