I haven't dated in a while and I'm on the fence if I should ask her out.

[Rider on the Storm]

Hello everyone. My apologies in advance for feeling completely clueless and having to seek direction from strangers on a forum when it comes to the subject at hand. Know that I appreciate you taking the time to read this and would certainly appreciate the feedback.

A little about myself.. I'm an early 40s divorcee. For two years (post marriage) I was in a relationship with a friend from my past that ultimately didn't work out. I've been officially single for several months now. I feel like this is the first time since my late 20s that I have actually been single (if that makes sense).

There is this woman in her mid 30s that works in management at a local small business that I frequent. I've known of her for about a year now. Outside of always thinking she was cute, I never gave the situation any further thought given my relationship at the time. And truth be told, up until a few months ago, I had assumed that she was married (she's not and never has been).

We have made small talk here and there throughout the year that I've known of her, but recently I have gone more out of my way to talk with her in an attempt to get to know her better. One day I even brought her a coffee to her at work after she had told me how tired she felt (she seemed to appreciate that). Anyway, given her job we usually have little time together, but I try to make the most out of the time that I do have with her. Recently, I have had a couple of opportunities to talk with her for about 15-20 minutes, uninterrupted. During that time we talked (surface level) on a variety of subjects to include her parents, her interest in traveling, her job, and she inquired what I did for a living, and asked me about my daughter.

Over the past few weeks I have left her store feeling slightly confident on some days (in terms of thinking that i might have a shot at a date), and on others days I felt less confident (kind of like this possible reciprocated feeling is probably just all in my head). Bear in mind, my lack of confidence isn't due to anything that she did wrong. I guess on some days there was just more opportunity to talk than others. Or maybe there was just more time or interest on her part. I really don't know.

A few highlights that have given me some optimism (although maybe this is just her way of being nice):

1.) One day one of her employees was helping me when she came up and told them that she could assist me (best I could tell there was really no reason for her to do this).

2.) During my recent 15-20 minute uninterrupted discussion, I mentioned having a brief business trip and a personal weekend trip within a matter of days of one another. During the discussion (and at 2 different points) she asked when I would be returning from the personal trip and when I would be returning from the business trip. Maybe this was just her being conversational?

3.) I am a member of a club within my area and one day I very casually mentioned "maybe I could invite you to be my guest sometime" to which she replied "ok".

4.) When she sees me she does always seem to make a point of smiling and waving. Although I understand that this could also mean nothing other than she is nice person.

5.) She has told me that I am "sweet", but I don't know if that is a good thing.

With all this said, I can't say that she has ever been outright flirty, although she is at work and she does strike me as a professional individual. She has always been nice and friendly to me.

Believe me, I completely understand that she is at work and the only way to know for sure would be to ask her. Obviously, I guess it's the possibility of rejection that is holding me back. Based on my above dissertation, could she be interested? Is she just being nice? By nature, I'm a pretty unassuming person and not very good when it comes to knowing the difference. Whether she could be interested, or is just being friendly, I am definitely interested in and attracted to her.

Again, please excuse my naivety and remember it's been a while since I've been single and even thought about asking someone out. Thanks for taking the time to read. I'd like to hear your feedback!

[salparadise]

28 minutes ago, Rider on the Storm said:

Obviously, I guess it's the possibility of rejection that is holding me back. Based on my above dissertation, could she be interested?

Of course she's interested. Otherwise she wouldn't be asking questions and chatting you up. You just have to suck it up and ask. What do you have to lose vs. what do you have to gain? There is a window of opportunity in these situations. If you wait too long it will close. Guys who get women are bold; they make the play in spite of anxiety or whatever. Just ask to meet for a drink after work or something easy. You can then ask for a real date when you have time alone. You miss 100 percent of the shots you don't take. Let us know how things go. 

[Wiseman2]

Yes. Ask her out. You seem ready to date after a brief postdivorce rebound situation.

You need to chitchat and get to each other on your own time, not her work time.

[glows]

11 hours ago, Rider on the Storm said:

Based on my above dissertation, could she be interested? Is she just being nice?

She seems open and receptive when you approach her from your account of things but you won’t know if she’s interested in going out or dating you unless you ask. 

This may or may not work out so don’t take it too personally either if she says no. Ask her out sooner rather than later and avoid building this up in your mind. Get it straight from her and see whether she accepts or declines. That’s the only way to gauge whether there’s some interest in dating you.

[Rider on the Storm]

12 hours ago, salparadise said:

Of course she's interested. Otherwise she wouldn't be asking questions and chatting you up. You just have to suck it up and ask. What do you have to lose vs. what do you have to gain? 

7 hours ago, Wiseman2 said:

Yes. Ask her out. You seem ready to date after a brief postdivorce rebound situation.

 

 

1 hour ago, glows said:

She seems open and receptive when you approach her from your account of things but you won’t know if she’s interested in going out or dating you unless you ask. 

 

 

Thank you, ALL. I sincerely appreciate the feedback. I know and agree that the only way to know for sure would be to ask. I'm sure I'm making too big of a deal of this, but I wish I didn't have to ask her while she is at work. I really have no idea if she will say yes or not. Like I said, I've left some of our conversations feeling somewhat confident (and probably should have asked at that time) while leaving other conversations feeling much less confident. 

Something that I failed to mention in my initial post and without going in to too much detail, several weeks back, during one of our brief conversations, she mentioned wanting to try something. As luck would have it, I know of a small business in town that I thought might have what she was looking for - or at least a suitable substitute. Anyway, several days later, I picked it up and gave it to her (it was nothing overly personal). She seemed genuinely surprised. I think her response was "no way". About a week ago, she brought up that, despite it not serving the purpose that she was hoping for, she still enjoys it. So, I'm only mentioning this because I assume that she probably knows that I at least somewhat like her.

Unfortunately, her place of work is somewhere that I have frequented almost daily for several years. If she turns me down, I think that will make for somewhat of an awkward scenario going forward. I'm going to have to psyche myself up to do this.

Edited August 5, 2022 by Rider on the Storm

[salparadise]

1 hour ago, Rider on the Storm said:

I'm going to have to psyche myself up to do this.

Well, I'd say try and do sort of the opposite... tone down the psyche so that you don't feel anxious, and so that she doesn't pick up on nervousness. I understand it's not easy to get into the right headspace. I just think you need to be less invested in outcomes and more c'est la vie. It's not like anything huge is at risk here other than momentary disappointment. This is why I suggested to ask her to grab a drink or something easy, and also because if you have to ask while she's at work you don't want it to have to go into a lot of detail. The self-talk should be, "no big deal, just ask." Based on what you've said, and the fact that you've already shown interest and she's still engaging, I'd guess that the odds are way in your favor. 

Edited August 5, 2022 by salparadise

[Rider on the Storm]

1 hour ago, salparadise said:

Well, I'd say try and do sort of the opposite... tone down the psyche so that you don't feel anxious, and so that she doesn't pick up on nervousness. I understand it's not easy to get into the right headspace. I just think you need to be less invested in outcomes and more c'est la vie. It's not like anything huge is at risk here other than momentary disappointment. This is why I suggested to ask her to grab a drink or something easy, and also because if you have to ask while she's at work you don't want it to have to go into a lot of detail. The self-talk should be, "no big deal, just ask." Based on what you've said, and the fact that you've already shown interest and she's still engaging, I'd guess that the odds are way in your favor. 

Yep. You're 100% right. Thanks for being a voice of reason when I can use one!

[Rider on the Storm]

On 8/5/2022 at 1:03 PM, Rider on the Storm said:

Yep. You're 100% right. Thanks for being a voice of reason when I can use one!

SO, a little update to anyone who might be reading. I told myself the next time I have an opportunity to talk with my crush privately for a few minutes (and the conversation seems to be going well), I'm going to ask her if she might like to grab a bite to eat. Fortunately, I saw her today, but unfortunately, the store that she manages was crazy busy and for the brief few minutes that I did see her we were surrounded by others. 

With that said, I went in and ordered lunch to go. We saw one another and she gave me one of her incredible smiles and waived as she was running around doing something. She said something (I think it was related to me being in there for lunch), but I couldn't quite make out what she said exactly, so I just kind of smiled and nodded my head. Anyway ..a few minutes go by and as the gentleman was getting my order together and began to ring it up, I noticed that she came up to him and said something, while signaling towards my direction. Knowing that she had my attention, she said something along the lines of "this is on me" - and she attached a paid receipt to my order. 

I told her that she absolutely didn't have to do that. She said it was her way of saying thanks (as previously mentioned, I had brought her coffee on a couple of occasions when she mentioned being tired, and one other gift that wasn't overly personal, but something that she had mentioned wanting to try). I reiterated that they were gifts and that I didn't expect anything in return. She said, "this is my gift to you".

Whether or not it's indicative of anything else, I thought it was really thoughtful of her and it was certainly appreciated on my part. Honestly, made my day!

SO, could this be considered a sign of potential interest? Should I not read into it any more other than her being nice and saying thanks for previous things that I had brought her?

Whichever it may be, I would appreciate your thoughts!

[Weezy1973]

19 minutes ago, Rider on the Storm said:

SO, could this be considered a sign of potential interest? Should I not read into it any more other than her being nice and saying thanks for previous things that I had brought her?

Whichever it may be, I would appreciate your thoughts!

You just have to ask her out and not worry about signs of potential interest. Although I understand the anxiety attached to asking someone out, you’re much better served to detach from the outcome. Basically you’re either going to get a yes or a no, but the kicker is both of those answers are good. If it’s a yes, great you have yourself a date with your crush. Doesn’t mean you’re compatible at all long term, but dates can be fun regardless. And if it’s a no, great as you can move on from your crush and open yourself up to possibilities with other women you likely weren’t noticing due to your crush…

[Wiseman2]

26 minutes ago, Rider on the Storm said:

I thought it was really thoughtful of her and it was certainly appreciated on my part. Honestly, made my day! SO, could this be considered a sign of potential interest?

Yes, its a green light to finally ask her out. Maybe she doesn't date customers or has a BF but whatever the case, you'll have to take the leap.

[Rider on the Storm]

So, no "significant" update to make, but I did have somewhat of an odd couple of days that I would like to get some feedback on.

I have yet to ask my crush out. She was off the past couple of days and while I did see her very briefly today, she was occupied with others and I'm not even sure that she saw me. As mentioned, if and when I get another opportunity to speak with her alone (as I have a couple of times now) - and assuming the conversation appears to be going well - I AM going to bite the bullet and just ask her if she'd be interested in dinner. However, on to the odd ..

Given that I go to the same place daily for lunch, I somewhat "know" many people there. At least from a surface level standpoint. Anyway., I was ordering lunch on Monday and myself and the gentleman putting it together for me was shooting the breeze (he's a guy that I vaguely know from going in there). I can't recall what we were even talking about, but at one point (for no obvious reason) he comments to me: so-and-so (my crush) isn't working today. Again, we weren't talking about her, so I'm not sure why he brought her up. Another co-worker of his (who I happen to chat with as well when I go in there) commented "did you hear that so-and-so (my crush) will probably be leaving this specific location soon due to a potential promotion. I WAS aware of this. She had mentioned this to me during one of our 15 minute chats a couple weeks back. While the possibility exists that she will be leaving this specific location at some point, she will go to another store in the same geographic (likely 20 mile radius) area. I didn't find the co-worker's comments too odd since he was just commenting on the other guy mentioning that she was off today.

On to yesterday .. I'm in there ordering lunch and the lady that was putting it together for me is someone that I talk with on occasion once or twice per week. Her, I, and another lady (who I think was another customer) were talking about whatever. Somehow the conversation went to online dating. I commented that I have never done that and I doubted that it would be for me. The lady who works there agreed that it wouldn't be for her either and commented to me "wouldn't you rather just come somewhere like here and potentially meet a person you are interested in organically". I don't consider that to be OVERLY odd, but figured I'd throw it in since it was said.

On to today..  this specific interaction raised the most question because of what this specific employee said to me (totally different individual that anyone referenced above). If his comment was sincere, it would put the idea to bed once and for all, in terms of me getting to know her better. So here is what happened... I'm talking with this younger guy that works in there (we shoot the breeze on occasion as well). Anyway, today was his last day of work for a week because he and his girlfriend were going on vacation. He had commented to me that his girlfriend was funding the majority of the trip and I asked him how the heck he pulled that off (jokingly) . When I asked what she did for a living he told me and said "she used to work here. You probably know her." He said her name but I said I wasn't sure. He showed me a pic of her, but I still couldn't say whether I had ever seen her or not. I made the comment to him, "so you met her here? Sounds like a nice office romance (he and I have the kind of relationship where I felt like I could say this). The guy who works as a Lead/Supervisor type was standing next to him and I said to him, "so is this the type of stuff that you allow to happen here (again, just joking). He commented, "I can't talk .. I actually met my wife working here." Right after saying that the younger guy who I was initially talking with commented, "Yeah .. and so-and-so (my crush) met her boyfriend while working here too". He gave me this half smirk thing as he said it to me.

SO, I know this is a mess of a post, but I am 50/50 on this younger guy's comment. I don't know if he was making the implication that *I* am her boyfriend, or if he was being sincere that she actually DOES have a boyfriend that she met here. Like I said, I think it's fair to say that he and I have been jabby at one another in the past, so I think it's possible it could have been a friendly jab at me, but I don't know that either. Again, seems kind of odd that he brought her into conversation.

In the couple of years that I've been going in there and the couple of years that she has been there, no one else has ever brought her up in conversation to me, to the best of my recollection. I just find it odd that in a course of a few days, there were at least 2 comments where she was brought into the conversation by others, and then another comment that may have been coincidental, but still kind of odd, nonetheless.

Initially I was a bit taken back by several of the comments because I wondered why they would bring her up to me. The more I thought about it though, the more I came to the conclusion that maybe our 10-15 minute discussions, me bringing her coffee on a couple of occasions, and some light hearted public banter between her and I may not have went unnoticed by others? I guess? Maybe I'm more obvious that I imagined? I really don't know.

I do value the feedback that I have received here thus far. I feel as if it keeps me grounded.  SO, what do you think? Am I just reading into things that aren't there? I know it's impossible to say if the younger guy was taking a jab at me or being sincere, but in the conversations that we have had, my crush has had the opportunity, but never made mention of a boyfriend. I had finally talked myself into just asking her the next opportunity that I got. Now I feel as if I may need to start the question by saying "Hey. I have no idea if you have a boyfriend, but if not ..." Is that how you ask? 

Any thoughts or feedback whatsoever would be appreciated! For those that read this whole crazy long-winded post, thank you!

 

 

[assertives]

Just ask her out and you will know the answer. Don't waste so much time micro analysing everything. It'll just build even more inertia. If she says no, or tells you she's taken, well, she's moving away to somewhere else soon, so it wouldn't be too awkward.

No one including those characters you brought up can tell you what's going on in her mind. I do believe that there's a window of time for this kinda thing. If you sit on it enough and don't ask her out, the interest and curiosity will eventually fizzle out.

Edited August 11, 2022 by assertives

[Wiseman2]

8 hours ago, Rider on the Storm said:

  "Hey. I have no idea if you have a boyfriend, but if not ..." Is that how you ask? 

It probably wouldn't be a good idea to use an opening line like that.  It's a bit presumptuous. You seem to be confused about what to do with this. That's ok. Some things are better left alone. 

[introverted1]

On the plus side, you have nothing to lose, especially since she will be transferring to a different location soon.

On the other hand, you are far too anxious and in-your-head about this.  Ask her out.  If she says yes, great.  If she says no, no big deal.  You are not asking for her hand in marriage, just drinks (or whatever).  Stop imbuing it with so.much.meaning.

But honestly, it's time to either do it or move on.  You are tying yourself into knots trying to read into every word and glance.  This is not healthy and definitely not productive.

[Rider on the Storm]

SO, Bad news / good news (I suppose) ..

She has a boyfriend. The good news being, I did not have to ask her out to learn that. As usual, I went in for lunch today. She was busy doing her thing, but she saw me and started to engage me in some light conversation. Long story short, I eventually asked if she was able to plan the girls weekend that she was hoping for (that we had discussed previously). She told me that she has not been able to, but has a trip planned to go up north. I decided to use that opportunity and confirm if that was the girl's trip that she was hoping for, or just a solo mission. That is when she responded, "actually my boyfriend's ...".

I'm going to lie, that initial mention did sting a bit, but at least I know now (and I didn't have to go as far as asking her out to actually learn that).

She certainly never "owed" me that information by any means (and I do realize that), but I will say, in retrospect, I am a little surprised that the boyfriend was not brought up sooner.  It seems like we chatted enough and about enough surface level topics that a boyfriend may have been mentioned before this. Even today, had I not pushed with "are you going with friends or ..", I'm not sure that she would have even mentioned him. But again, not that she had to. 

Anyway, while disappointing, at least I can move on from this now and it didn't result in me having to ask her out to learn this.

I do appreciate everyone's feedback here. It definitely helped. 

 

[Wiseman2]

2 hours ago, Rider on the Storm said:

Bad news / good news (I suppose) ..She has a boyfriend. The good news being, I did not have to ask her out to learn that.

But the really good news is now you can free your mind to date other women without this running in the background.

[smackie9]

My advice, no matter what confidence always wins in the end. If you find someone attractive, you ask them out after meeting them. If she has a BF who cares, they will be flattered anyways...and to boot, they will remember it. Down the road when they are single again, you will be the first one they think of. I'm tell you this from a woman's perspective. I never had much attraction for a guy that hovered around, looking at the ground or shying away. A guy that can just go right up and show his interest, is quite emotionally simulating to a females brain, even if you are average looking. I just love a man's confidence. 

[glows]

2 hours ago, Rider on the Storm said:

SO, Bad news / good news (I suppose) ..

She has a boyfriend. The good news being, I did not have to ask her out to learn that. As usual, I went in for lunch today. She was busy doing her thing, but she saw me and started to engage me in some light conversation. Long story short, I eventually asked if she was able to plan the girls weekend that she was hoping for (that we had discussed previously). She told me that she has not been able to, but has a trip planned to go up north. I decided to use that opportunity and confirm if that was the girl's trip that she was hoping for, or just a solo mission. That is when she responded, "actually my boyfriend's ...".

I'm going to lie, that initial mention did sting a bit, but at least I know now (and I didn't have to go as far as asking her out to actually learn that).

She certainly never "owed" me that information by any means (and I do realize that), but I will say, in retrospect, I am a little surprised that the boyfriend was not brought up sooner.  It seems like we chatted enough and about enough surface level topics that a boyfriend may have been mentioned before this. Even today, had I not pushed with "are you going with friends or ..", I'm not sure that she would have even mentioned him. But again, not that she had to. 

Anyway, while disappointing, at least I can move on from this now and it didn't result in me having to ask her out to learn this.

I do appreciate everyone's feedback here. It definitely helped. 

 

It seems odd that she never mentioned a partner earlier and was so friendly with you. That would be a huge turn off. You seem to just be getting back out there. You’ll gain more confidence with time the more people you meet and as time goes on.

Edited August 11, 2022 by glows

[Rider on the Storm]

2 hours ago, Wiseman2 said:

But the really good news is now you can free your mind to date other women without this running in the background.

Thanks Wiseman. Your feedback was both consistent and blunt throughout. It was both valuable and appreciated on my end.

1 hour ago, smackie9 said:

My advice, no matter what confidence always wins in the end. If you find someone attractive, you ask them out after meeting them. If she has a BF who cares, they will be flattered anyways...and to boot, they will remember it. Down the road when they are single again, you will be the first one they think of. I'm tell you this from a woman's perspective. I never had much attraction for a guy that hovered around, looking at the ground or shying away. A guy that can just go right up and show his interest, is quite emotionally simulating to a females brain, even if you are average looking. I just love a man's confidence. 

Thanks smackie. I totally agree. In retrospect, and whenever I find someone in the future who might catch my eye, I will dwell less and be sure to ask the question sooner rather than later. The funny thing is (and this is not at all obvious by my posts in this thread), I actually do consider myself a confident individual, generally speaking. I don't think I'm bad looking, I probably look a little younger than I actually am, I think I'm a good Dad, and I have a good career. The majority of people that I know would probably refer to me as a social type before they'd consider me a shy, introvert type.

In this scenario, the 3 things that caused the most self doubt was:

1.) I'm guessing that I'm about 10 years older than her. I didn't know if that would be an instant deal breaker.

2.) I never loved the idea of having to ask her out while she was at work. I didn't want that to come off as appearing weird or wrong.

3.) Lastly, just the obvious fear of rejection and  knowing so many people at her place of work. I found it especially tough to overcome that one.

1 hour ago, glows said:

It seems odd that she never mentioned a partner earlier and was so friendly with you. That would be a huge turn off. You seem to just be getting back out there. You’ll gain more confidence with time the more people you meet and as time goes on.

Thanks glows. And thank you for thinking that this did seem "odd" too. I'm not mad, but I am slightly disappointed that this didn't come up sooner. I'm not claiming that we had some great love affair where we were constantly talking and texting, but there were several extended conversations where she seemed equally as interested in the discussion. She talked to me a little about her family, where she grew up, her job, inquired on more than one occasion about my child (seeming like she had genuine interest), asked about my job, asked if I ever cook (lol), etc. I brought her coffee on a couple of occasions and one other gift; all of which seemed appreciated on her end. She even returned the favor and paid for my lunch. On more than one occasion, it seemed as if she almost went out of her way to come and talk to me.

Like I said previously, she definitely doesn't "owe" me any information, but it seems like she could have slipped in "my boyfriend and I" somewhere into one of those conversations prior to this. I know I'll never know why she didn't, but it would be nice to know the answer to that.

Such is life ..

[alphamale]

On 8/4/2022 at 8:47 PM, Rider on the Storm said:

Hello everyone. My apologies in advance for feeling completely clueless and having to seek direction from strangers on a forum when it comes to the subject at hand. Know that I appreciate you taking the time to read this and would certainly appreciate the feedback.

A little about myself.. I'm an early 40s divorcee. For two years (post marriage) I was in a relationship with a friend from my past that ultimately didn't work out. I've been officially single for several months now. I feel like this is the first time since my late 20s that I have actually been single (if that makes sense).

There is this woman in her mid 30s that works in management at a local small business that I frequent. I've known of her for about a year now. Outside of always thinking she was cute, I never gave the situation any further thought given my relationship at the time. And truth be told, up until a few months ago, I had assumed that she was married (she's not and never has been).

We have made small talk here and there throughout the year that I've known of her, but recently I have gone more out of my way to talk with her in an attempt to get to know her better. One day I even brought her a coffee to her at work after she had told me how tired she felt (she seemed to appreciate that). Anyway, given her job we usually have little time together, but I try to make the most out of the time that I do have with her. Recently, I have had a couple of opportunities to talk with her for about 15-20 minutes, uninterrupted. During that time we talked (surface level) on a variety of subjects to include her parents, her interest in traveling, her job, and she inquired what I did for a living, and asked me about my daughter.

Over the past few weeks I have left her store feeling slightly confident on some days (in terms of thinking that i might have a shot at a date), and on others days I felt less confident (kind of like this possible reciprocated feeling is probably just all in my head). Bear in mind, my lack of confidence isn't due to anything that she did wrong. I guess on some days there was just more opportunity to talk than others. Or maybe there was just more time or interest on her part. I really don't know.

A few highlights that have given me some optimism (although maybe this is just her way of being nice):

1.) One day one of her employees was helping me when she came up and told them that she could assist me (best I could tell there was really no reason for her to do this).

2.) During my recent 15-20 minute uninterrupted discussion, I mentioned having a brief business trip and a personal weekend trip within a matter of days of one another. During the discussion (and at 2 different points) she asked when I would be returning from the personal trip and when I would be returning from the business trip. Maybe this was just her being conversational?

3.) I am a member of a club within my area and one day I very casually mentioned "maybe I could invite you to be my guest sometime" to which she replied "ok".

4.) When she sees me she does always seem to make a point of smiling and waving. Although I understand that this could also mean nothing other than she is nice person.

5.) She has told me that I am "sweet", but I don't know if that is a good thing.

With all this said, I can't say that she has ever been outright flirty, although she is at work and she does strike me as a professional individual. She has always been nice and friendly to me.

Believe me, I completely understand that she is at work and the only way to know for sure would be to ask her. Obviously, I guess it's the possibility of rejection that is holding me back. Based on my above dissertation, could she be interested? Is she just being nice? By nature, I'm a pretty unassuming person and not very good when it comes to knowing the difference. Whether she could be interested, or is just being friendly, I am definitely interested in and attracted to her.

Again, please excuse my naivety and remember it's been a while since I've been single and even thought about asking someone out. Thanks for taking the time to read. I'd like to hear your feedback!

RotS, you’re allowed to ask a female out after 10 minutes of conversation, look at the anxiety this has caused you over time. That being said RotS, if a girl likes you, you’ll definitely know.