Should I have handled this scenario differently?

[SunglassesAtNight]

First and foremost, I appreciate everyone that takes the time to read my post and respond. 

I’ll start by saying, if someone were to tell me  that they were falling for their bartender, I’d roll my eyes and tell them that they are crazy ten out of ten times. With that said,  here’s my scenario ..

A couple of months back, I met and started talking to a bartender at a local, upscale bar and grille. On average, I see her a couple of nights per week. From the beginning, I thought she was extremely beautiful, but there was never any real intent on my part to pursue her romantically. I’m a pretty pragmatic individual by nature. Generally speaking, I know better than to try and hit on a beautiful bartender. With that said, we did seem to click well, had similar interests, a similar sense of humor, and she had a side business that genuinely interested me. 

About 3 to 4 weeks into this 2 month period, I noticed she seemed a little off one day and I asked her if everything was ok.  She mentioned that she was a little sad because she intended to break it off with this guy that she is seeing. I won’t get into the details, but according to her, it just wasn’t working out. She mostly seemed bothered by the fact that he was a nice guy. I’m pretty sure they have been seeing each other for several months.  About a week later, I saw her and asked how everything was going in that regard. She told me that they had a good talk and that she was still seeing him. 

Throughout the two months, I found myself questioning if I was imagining certain things. For example, it wasn’t uncommon for me to look her way throughout the course of a night and see her looking back at me. She would typically hold the stare for a second or two before giving one of her incredible smiles. To witness this two to three times per night wasn’t uncommon. I also noticed I started receiving a “friends and family” discount on my checks. Also, when the opportunity would present itself, she did seem to gravitate back my way more frequently than she would with other patrons. She also joked with me one night about how she thinks of me every time she hears these certain songs now because her and I had talked about them at one point or another. She kind of rolled her eyes and gave me this cute smile as she said that. (And just to be clear, at no point did I ever feel like these actions were tip driven on her part. While I tip well, we’re not talking life changing, and the tip wouldn’t increase or decrease based on the amount that we would communicate). 

Over the last 2 to 3 weeks, my curiosity as to whether she may be interested continued to grow, mainly due to the following: On one occasion, I came in for dinner and a drink when she wasn’t working. One of her female co-workers said, “Oh. [insert her name] just asked me if I have seen you lately. On 2 other separate occasions, one being as early as last week, I stayed until close one night and she joined me on the other side of the bar for a drink. I would say the conversation was flirty, but nothing too over the top. One other frequent patron (who her and I are both friendly with), along with the restaurant staff, was still there and within ear shot of our conversation. *I also want to clarify that when I say I was there until close, this place closes fairly early. When I say I’m in there for drinks, it’s typically only 2 to 3 over a couple of hour period. I just want to be clear that none of this is happening overly late night and while intoxicated.

Several days to a week after this occurred, I was talking with this other frequent patron and he said, “you know that she likes you, right?”. Honestly, while that did seem like a possibility, I was never overly sure. I’m of the position that if a woman references a boyfriend or a “guy she’s seeing”, often times, that is to establish a boundary. So, even though there were potentially signs of interest on her part, I can’t say that I was ever overly confident in knowing that. He also told her that he could tell that I was interested in her too. According to him, she responded by asking why I haven’t expressed this to her if that was the case.

Fast forward another several days to a week later .. there was another scenario where I was there until close, and she joined me once again on the other side of the bar for a drink. This time, I felt like she tried to pin me down a bit in terms of the questions she was asking. She referenced a couple of scenarios over a this couple month period where 2 separate women were coming on to me at the bar. I did not pursue these women in either instance. She wanted to know why that was. She also wanted to know why, of all the bars in the area, I chose this bar to frequent. She pushed by asking, “do you really just like {named my drink of choice} here that much?”. This was said with a smile on her face. 

Despite her knowing that I like her, I never did explicitly confirm this. I would chalk this up to several reasons (in no particular order): 1.) the guy that she’s seeing. 2.) a staff member was sitting right behind us and I’m sure he could hear everything that was being said, and 3.) several years ago, I went out on a couple of dates with a lady who had just come out of a relationship (foolish on my part). A long story short, I felt like she used me to get back with her ex-boyfriend. While I don’t see the situation with this woman and the situation with that woman being one in the same, that experience has always stayed with me and made me much more cautious any time I hear, “recently broke up”, “guy I’m seeing”, etc.. 

Fast forward to just last week… Following our encounter when she tried to pin me down a bit in regard to my interest, and her (probably) being the most visibly flirtatious that she has been, I saw her and things seemed notably different. While her and I made eye contact when I walked in, I didn’t note her usual smile. While we eventually spoke, things just seemed a bit off. At one point a week or two back, she mentioned that she thought that her and I have a good energy. I agreed with her. This particular evening did not feel that way. During our brief discussion, she mentioned that she was going to be going on a trip with “the guy she is seeing”. It hurt a bit to hear, but I wasn’t shocked either. She didn’t seem to sound overly enthusiastic about the trip (at least not to me), but I did tell her that I thought she would have a good time.

Later that same night, the other frequent patron joined me for a drink. He said he saw when I walked in and also noticed her demeanor when she saw me. Despite him maintaining that she likes me,  I reiterated that she has a boyfriend that she is about to vacation with, and as a result, I did not intend to pursue her. He told me that I came up in conversation after her and I last spoke. She told him, “He’s too late”. Despite this, he still insisted that she does like me and he did not see the current relationship of hers lasting.

With this post, I think I'm just trying to process the last couple of months. It was never my intent to fall for the bartender, or for things to take the turn that they did. I got to know her and genuinely liked her. I thought she was interesting, unique, kind, intelligent, and again, she is definitely beautiful.

I ran this scenario by 2 close friends. My male friend insisted that I should have let her know how I felt about her, regardless of the “guy that she’s seeing”. He said that’s not the same as having a ring on her finger, and I had no one to blame but myself. Ironically, my female friend had the opposite opinion. She agreed that by “seeing a guy” that establishes a boundary. She said that if she was interested in more than just a friendship with me, she had the option of ending her current relationship, and her and I could have went from there.

What do you think? Should I have handled this differently? A part of me feels like I handled it correctly by not overly pursuing her. Admittedly, another part of me does regret not being more forthright about my feelings for her. I do like her a lot, but I didn’t want to open up like that just to have her potentially reiterate her relationship and have this entire scenario turn into a very awkward situation. Sadly, I’m thinking that the best path forward may be to take an extended hiatus from this place and that situation in general. 

How would you have handled this? Any and all thoughts and feedback would be greatly appreciated.

[Gaeta]

Too little, too late.

She practically threw herself at you and you did not reciprocate so she assumed you're just one of those guys sitting at a bar.

To me *seeing someone* is not the same as being in a relationship. It's the equivalent of casual dating. 

Edited December 2 by Gaeta

[SunglassesAtNight]

19 minutes ago, Gaeta said:

Too little, too late.

She practically threw herself at you and you did not reciprocate so she assumed you're just one of those guys sitting at a bar.

To me *seeing someone* is not the same as being in a relationship. It's the equivalent of casual dating. 

Thank you, Gaeta. I’m not going to lie. That does suck to hear, but I appreciate the feedback just the same. 

Despite it likely being too late, a part of me wonders if I should reach out to her? Even though I agree it probably is too late, I’d like her to know that my intent wasn’t to brush her off, or to make her feel any certain way. She actually is a really cool lady and I can’t help but to feel bad about all of this. To me, it’s either do that or just stop going there in altogether.

I’m not sure what’s wrong with me. I think it comes down to having an unusually high fear of rejection. That’s the only way I can explain it. 

[Acacia98]

You did the right thing. There's no way I'm gonna keep dropping hints about liking someone if I've established a boundary by stating that I'm dating someone else. If I want a guy to ask me out, I'll make sure he knows I'm available.

Anyway, I think your dating philosophies are rather different. So even if you asked her out and she agreed, things wouldn't work out between the two of you in the long term because you care about boundaries and taking time to recover between relationships and all that good stuff and she doesn't seem to think too deeply about all of that. Definitely take a break from visiting that establishment.

[Gaeta]

1 hour ago, SunglassesAtNight said:

Despite it likely being too late, a part of me wonders if I should reach out to her? Even though I agree it probably is too late, I’d like her to know that my intent wasn’t to brush her off, or to make her feel any certain way. She actually is a really cool lady 

If you want to reach to her just to tell her something passive like you did not mean to reject her then no, it's not worth it.

There is no rush, you don't need to make any type of decision. Going on a trip when the relationship isn't going well has a way to speed up the end of a bad relationship.

 

[SunglassesAtNight]

1 hour ago, Acacia98 said:

You did the right thing. There's no way I'm gonna keep dropping hints about liking someone if I've established a boundary by stating that I'm dating someone else. If I want a guy to ask me out, I'll make sure he knows I'm available.

Anyway, I think your dating philosophies are rather different. So even if you asked her out and she agreed, things wouldn't work out between the two of you in the long term because you care about boundaries and taking time to recover between relationships and all that good stuff and she doesn't seem to think too deeply about all of that. Definitely take a break from visiting that establishment.

Thanks Acacia98. I appreciate it.  It sounds like you hear “I’m seeing someone” the same way that I hear it. I’m glad to know that I’m not alone. lol.

But to Gaeta’s point, I also think “seeing someone” has a different meaning that it did, say, 20 years ago. My understanding was always, if a lady tells you that she has a boyfriend, or that she is “seeing someone”, that’s a way to let others know that she is not available. With that said, I understand  that the latter doesn’t necessarily hold that same meaning these days. 

As far as our dating philosophies being different, I really don’t know. When coming out of a serious, long term relationship, I’ve always taken breaks after a relationship has ended. If I wasn’t overly invested in the relationship, and it was short term, I’m not sure that I would need that same hiatus. 

Thanks again for your feedback. 

Edited December 3 by SunglassesAtNight

[introverted1]

Either she was setting a boundary or she was looking to monkey-branch. 

Regardless, I think you should write this one off.

[Gaeta]

17 hours ago, SunglassesAtNight said:

but according to her, it just wasn’t working out. She mostly seemed bothered by the fact that he was a nice guy. I’m pretty sure they have been seeing each other for several months.  About a week later, I saw her and asked how everything was going in that regard. She told me that they had a good talk and that she was still seeing him. 

When a woman wants to breakup with a man but she doesn't want to hurt him because he's a 'good guy' it means she did not connect with him. I doubt she would need months to mourn this relationship. The other point is you 'assume' they have been seeing each other for several months, don't know what you consider 'several months' but that tells me this relationship did not reach the long term milestone. You spoke about this man she is 'seeing' more than once and has she ever referred to him as her boyfriend?

I better never catch my boyfriend talking about me in terms of 'the girl he's seeing'. 

[SunglassesAtNight]

5 minutes ago, Gaeta said:

When a woman wants to breakup with a man but she doesn't want to hurt him because he's a 'good guy' it means she did not connect with him. I doubt she would need months to mourn this relationship. The other point is you 'assume' they have been seeing each other for several months, don't know what you consider 'several months' but that tells me this relationship did not reach the long term milestone. You spoke about this man she is 'seeing' more than once and has she ever referred to him as her boyfriend?

I better never catch my boyfriend talking about me in terms of 'the girl he's seeing'. 

I don’t recall her having ever referred to him as her boyfriend. To the best of my recollect, she has only referenced him twice over a couple of month period: the time she was going to break up with him, and when she referenced this trip with him last week. In fact, she initially referenced him by name when she said they were going to take this trip. I probably looked a little confused because she followed up with, “the guy I’m seeing.”

I don’t know exactly how long they have been seeing one another, but I would definitely say months - not years - based on our initial discussion. That conversation was 3-4 weeks in of me getting to know her. In short, they dated briefly when they were younger. I think he was a neighbor, or classmate, or something. He always kind of liked her and they reconnected at some point within the past however many months. When she initially told me about him, she appeared  to regret that she let it go beyond it just being a friendship. She said something like, “it’s a guy who had a crush on me when I was younger .. if that tells you anything.”

[Acacia98]

20 hours ago, SunglassesAtNight said:

Thanks Acacia98. I appreciate it.  It sounds like you hear “I’m seeing someone” the same way that I hear it. I’m glad to know that I’m not alone. lol.

But to Gaeta’s point, I also think “seeing someone” has a different meaning that it did, say, 20 years ago. My understanding was always, if a lady tells you that she has a boyfriend, or that she is “seeing someone”, that’s a way to let others know that she is not available. With that said, I understand  that the latter doesn’t necessarily hold that same meaning these days. 

As far as our dating philosophies being different, I really don’t know. When coming out of a serious, long term relationship, I’ve always taken breaks after a relationship has ended. If I wasn’t overly invested in the relationship, and it was short term, I’m not sure that I would need that same hiatus. 

Thanks again for your feedback. 

You're welcome, SunglassesAtNight.

Here are my thoughts:

1. If I were seeing someone casually, I wouldn't bother mentioning it to a guy I wanted to ask me out unless I believed that the best way to get the guy more interested in me was to make him jealous. But maybe I'm missing something. Beyond setting a boundary and trying to inspire jealousy, can you think of reasons why someone would mention they were seeing someone to a potential love interest? And if you can think of other reasons, do they point to a mature, healthy approach to relationships?

2. If I were you, I wouldn't second-guess myself. It's not your job to rescue a grown woman from a relationship she has chosen to be in. And yes, it is a full-fledged relationship, or at least the man believes it is. In my experience, people don't stay in casual flings because they don't want to hurt the nice guy.

 

[MsJayne]

Mentioning a partner is usually a way of establishing a boundary, but speaking negatively about the relationship, (ie: mentioning that she's planning to break up with the partner), is a way of downplaying the importance of it. I'd proceed cautiously, if she's only staying with that guy while she waits for something better to come along that's not such an attractive trait. She's OK with not being honest with her partner, so that's something to ponder too. Maybe you should just continue going to that bar and being friendly with her, let her know that if she was single you'd ask her out, and try to find out why she stays with someone she's not really happy with. If she was happy with him she wouldn't be so obviously encouraging attention from you. 

[SunglassesAtNight]

6 hours ago, Acacia98 said:

You're welcome, SunglassesAtNight.

Here are my thoughts:

1. If I were seeing someone casually, I wouldn't bother mentioning it to a guy I wanted to ask me out unless I believed that the best way to get the guy more interested in me was to make him jealous. But maybe I'm missing something. Beyond setting a boundary and trying to inspire jealousy, can you think of reasons why someone would mention they were seeing someone to a potential love interest? And if you can think of other reasons, do they point to a mature, healthy approach to relationships?

2. If I were you, I wouldn't second-guess myself. It's not your job to rescue a grown woman from a relationship she has chosen to be in. And yes, it is a full-fledged relationship, or at least the man believes it is. In my experience, people don't stay in casual flings because they don't want to hurt the nice guy.

 

Thank you again, Acacia. Once again, your advice and feedback is appreciated. To answer your question, no,  I cannot envision a scenario where I would tell a potential love interest that I’m seeing someone, especially if I’m not even overly certain that I am into the person that I’m currently seeing. I think that would defy logic. 

I just don’t know. I really don’t. And it does bother me because I do like her. I don’t want to make her out to be someone who is flakey or disingenuous or anything like that,  because I don’t believe that to be the case. She’s actually really intelligent, interesting, and seems well grounded. She hasn’t ever said anything in the course of a 2 month period that I thought was out there. Right or wrong, maybe it’s just a matter of her wanting some companionship over no companionship. She wouldn’t be the first person I have met who has been like that.

I do think I flustered her that night when she was trying to pin me down to say how I felt. At one point,  I recall her just kind of looking down and shaking her head with this look of,  “I give up”. I remember that well. I think I may have upset her or made her feel a certain way. Whether that was the reason she told me that she was going to take this trip with him several days later, I have no idea. But to your point, “making me jealous” is as good as an explanation as any. I certainly don’t have any better. 

And I do agree with you that the vast majority don’t stay in relationships just to be nice. If I had to bet the farm right now, I’m guessing that she likes that this guy is good to her and she may just view it as companionship. Or maybe he is slowly winning her over. I don’t know. I do know that she was in a difficult relationship prior to this one.  
 

 

[Maldives]

When she gets back when it's the right moment ask her out and go from there. I wouldn't spell out how you feel just yet (it might backfire and scare her off) just dip your toe in the water first and see if she responds positively to a date and says yes. If she says yes that's a good sign. If she turns up and keeps the date that's even better. Then if you guys hit it off,  ask her out again In a couple days. Just get to know her outside the bar and have fun with her. Those first initial checkpoints will tell you if she's interested. If she turns down your date invitation, leave it for a few days and see if she follows up with an alternate date /time. Let her come to you. If she doesn't and a few days have passed, you can try one more time or not it's up to you but If she turns down a second date then I think you definitely know where you stand. Good luck and just ask her out on a date. What's the worst that can happen except for a lil rejection that'll pass. Better to try than live with regrets.

Edited December 4 by Goodguy05

[Miss Spider]

She was bothered by the fact he was a nice guy…..? Umm

Anyway, I know others have said it, but you are probably playing yourself a bit. I have a lot of bartender friends and that’s their job to be charming and gregarious. It gets them more regulars annd more tips. What you speak of  is such a well known delusion that it’s a cliché to fall for a  service industry person , whose literal job is to be friendly and hospitable

 

. You’re most likely  reading too much into her friendly interactions as a bartender because you are attracted to her. Now if you want to shoot your shot go ahead and do it . If you think you got it like that, you have as good as much a chance as anyone. It’s a bit different because I’m a chick(so maybe a lot less competition) but I slid a bartender my number one night and  we dated for a good while after haha.  I feel like you’ll regret the things you don’t do more than the things you do. You only live once. If you don’t ask, the answer is always “no” yadda yadda 

Edited December 4 by Miss Spider

[SunglassesAtNight]

17 hours ago, Miss Spider said:

She was bothered by the fact he was a nice guy…..? Umm

Anyway, I know others have said it, but you are probably playing yourself a bit. I have a lot of bartender friends and that’s their job to be charming and gregarious. 

You’re most likely  reading too much into her friendly interactions as a bartender because you are attracted to her. 

I may have phrased myself poorly when I initially posted, but she wasn’t bothered by the fact that he was a nice guy. When she initially told me that she was thinking about breaking up with him, she told me that it made it was somewhat difficult because he is a nice guy. 

Regarding me reading too much into everything because I’m attracted to her, I’m not going to dispute that anything is possible because who knows, but I do feel like that is somewhat unlikely. Even if I were to say that I’m so attracted that I’m reading more into her actions that are actually there, I would then  have to explain why this other frequent patron, who has ties to this place’s management and ownership, would be fueling the scenario by insisting that she likes me and telling her the same about me. Without going into details, I don’t believe that is something that he would do if it was totally untrue.

i appreciate your feedback.

 

Edited December 5 by SunglassesAtNight