[Dom1]

Thanks April. That was what I thought, enjoy what you have, don’t give up on it and see what happens. I have basically fallen in love with her, as much as I don’t want to admit it. So we had a little talk the other day before I read your advice. She had been really blowing me off for over a week. So I told her the situation between us was getting a little frustrating for me. She did have a lot going and if that’s all it was that’s ok, but I was getting the vibe that she wanted me to go the hell away, despite how good a time we had when we went out. Basically she said yeah, she has a great time spending time with me, but has the impression that I’m after more than she has to offer (re mostly liking girls), and that it feels a little selfish to hang out with me and encourage something that isn’t likely to happen. Like she would just be creating more frustration for me. And I got that. I told her what I told her before, that I had a totally reevaluated my intentions, and hanging out with someone that really makes me super happy is ok. If that’s all I get, than I should enjoy it, instead of being annoyed that it’s not perfect or exactly what I want it to be. Just enjoy it, for however long I can have it. I don’t know if that’s right, I really don’t. I don’t know if at this point in life I should still be looking for something that is exactly what I want it to be, or just be grateful when someone comes along that I’m attracted to, and like being around, and just try to enjoy it. Even if in the long run in very likely to get hurt or frustrated. Any thoughts on that?

[Dom1]

We went out a few times later and had a great time but nothing more. Then a few weeks ago I invited her to a concert in Brooklyn near her house. She gave me a maybe and I was sure she wouldn’t actually come but in the end she did. We went to her house got ready and went. Had an incredible time. Laughing and joking the whole time. And ended up making out. Usually you build these things up in your head and they don’t live up to the fantasy but this truly did. Same thing last weekend. We went out. Really great time and lots of kissing. This is the thing; it is like pulling teeth to get her to come out with me, I literally feel like I’m forcing her to do something she doesn’t want to do. I get told maybe, I might be free, we’ll see, things like that. But when we do spend time together it’s like we’ve been dating for months. We have a great time. Last weekend toward the end of the night I was walking her home and she made a comment about how good a job I’ve been doing courting her or whatever. I made a joke about thinking I’d been too persistent and probably should have given up. She said no I was doing good. So what does this girl want from me? We’re both in our early 30s, is hard to get still a thing? Do woman really want to be chased like this? Every time we’re together I learn more about her and what it’s like to be around her and I’m realize I have serious feelings for her, or at the very least, I’m really really happy when we’re together. Makes me happy for days after. When she’s blowing me off, I’m crushed. Really. Any advice or insight into what is going on here?

[Dom1]

So of course I have not taken your very sound and logical advice. This has become more of a place for me to journal about all of this anyway. After the initial “date” at which I had the bomb dropped on me we’ve gone out two more times. Once last week and again last night. We had a decent time last week but last night was so much fun. Again. On the advice of another female co worker. I literally ignored her all week. The test was see if she initiates anything when I just hang back. Which she did not. I was supposed to do it for at least a week. I made it just short of 3 days. I was going to look at an apartment in her neighborhood in Brooklyn. It seemed like a perfect opportunity to see her and I guess I was too weak to just let it pass. So I texted her and told her I’ll be in the area in the evening and that she could show me a place to get a drink if she was free. She had tentative plans with a friend. So whatever. I wasn’t holding my breath. I get done seeing the apartment and let her know I’m done. She texts me right back and picks a place and we meet. I’m really surprised every time this girl hangs out with me because I can’t think of a reason why she would want to aside from liking me to some extent. I’ve stopped treating her like a girl I’m trying to “court” or whatever because it’s easier to just be myself because what’s the difference at this point. And I’ve found its really easy to be myself around her. We talk non stop and tease each other and touching a tiny bit. This girl does not stop staring into my eyes the whole time we’re together and everything about it just screams to me this girl likes you! There were a couple moments where it got quiet for a moment and I could have or should have kissed her. Including when we said goodbye. I went to give her a little hug, just a hug, and she came into it like I was gonna kiss her, I think, and seemed like she was gonna go with it. But just a hug. I was not prepared for that. I haven’t been so unsure about what’s going on with a girl so badly in a long time. Going in for kiss is kind of going all in. If you’re wrong there’s really no coming back from that. It might be about the most embarrassing thing that could happen. If I’m wrong I’m turning a moderately awkward situation into one that would be just awful.
I change my mind by 180 degrees no less than twice a day. Starting just a few seconds after I wake up. Before my feet even touch the floor. The situation seems to change non stop. In the span of a week I’ll be completely convinced that I’m absolutely irritating this girl, she can’t stand me, she’s into me but uncertain, she’s into me and wants to hang out with me and probably wants me to kiss her! The whole spectrum back and forth, it’s crazy…
Yeah that’s where I stand I guess.

[Dom1]

I’d say that’s pretty accurate. I have been know to bang my head against the wall of reality until I’m just to hurt to keep doing it. I know your advice is correct for two reasons: leaving her alone and moving on is likely the only way I’d ever beat those terrible terrible odds (which is what I should have done in the first place), and if it doesn’t change anything, eventually I won’t just be acting, I will have actually moved on. In trying April I honestly am. It’s really difficult to do when I’m at work with her for 10 hours a day but I’m going to keep trying. Another female coworker told me I’ve become her “work friend”, and I know exactly what that means, someone we help pass the somewhat tedious or stressful times at work, or chat with when we take a break. It turned my stomach. I am definitely not her work friend, and as I told her, not interested in being her actual friend. Makes me sound like Akeem but it’s true. Thanks for your help April. As with many other people who have tried to give me advice, I should have listened to you from the beginning.

[Dom1]

So I attempted to take your advice, but of course didn’t because I’m stupid and weak basically. Last Tuesday I said to her something pretty close to “so are you gonna let me buy you a drink or what?” Her very quick answer was yes. After work there was some confusion about whether I meant that night or another and I didn’t know what I meant myself. So we go to have one drink. One. Which turned into about 4. We talked and cracked each other up for about 3 hours. I haven’t enjoyed someone’s company like that In a long time. I felt relaxed and had a lot of fun. At one point after telling her some stories about exes and relationships I asked her what was so complicated about her situation. She says she’s been involved in a long distance thing she never planned for the past few months. I say that’s really not all that complicated for people our age. Then she tells me, well, it’s with another woman. Jesus Christ.
I don’t now if suddenly it all makes a ton of sense or just got infinitely worse. She says she’s mostly been in long term relationships with girls, more short term with guys. Like 60/40 she says. I’m basically stunned and don’t know what the hell to say, once again. We continue with our night after a few more questions and really just have an awesome time. She’s not exclusive or committed but told me she didn’t know how I’d react to that. She also said she was oblivious to the fact that I liked her until I got her the book and didn’t know what to do when I asked her out. It’s not a secret at work but it’s also no ones business either who she sleeps with.

So if I wasn’t lost before I certainly am now. I mean honestly. I seriously didn’t know such a thing existed in real life. And so you are so so right April. I want her way more now. Part of it is because I got to know her much better that night and we had the longest conversation we’ve ever had and it was better than I even hoped for. But I’ll admit it must at least partly because she’s all the more unattainable. So. No advice needed. I tried a couple days later to take her out again and we started walking together after work and she decided she wanted to go home instead. Blah. The only answer I have at this point is to try to never ever talk to her again. That sucks huh.

[Dom1]

I guess I want to know what to do/what the hell is wrong with me!

Same thing again yesterday. Work girl wants to take little breaks just me and her. We both work super late. And when a couple of us want to get a drink afterwards, and she knows I want her to come, it’s no thanks I’m gonna head home. I just don’t get it. Every little ten or 20 minute session of alone time I get with her makes me genuinely like her more and more and want to know her better. I haven’t built her up to be some perfect women but every detail I find out about her and her life, I like. Makes me think more of her and makes me affirm my initial thought that this is the kind of girl I want to be with. And at the same time I’m feeling more and more guilty because I’m falling for someone I can’t have (at least thus far) and it’s ruining my time with a fantastic girl who is crazy about me. I could have not worked last night. Jane wanted to go to dinner. I sort of volunteered hoping I’d get to go out with work girl when we were done. Pathetic I know. My inclination now is to lay it out for her one more time, and tell her this is kind of it, I want to take you out and i really like you and I’m drawn to you, but I can’t keep asking you and not have it happen (every time it comes up there is some reason she can’t hang out when I’m asking her too, not the it’s complicated thing stopping her. I don’t know if that means she’s just being super polite or what, or if it’s her being indecisive and not wanting to totally put me off). So this it, if you can’t make up your mind and come out for a drink with me, someone you seem to be happy to spend time with, or I am basically giving up. Thanks and good luck and sort of leave me alone at work from now on. I know that’s almost definitely the wrong thing to do but that’s what I’m leaning toward.
So yeah. What is wrong with me and what the hell do I do.

[Dom1]

Hi April. You’re probably getting tired of my whining but I’ve found you’re advice to be really insightful and helpful and there is another layer to this story I haven’t mentioned and I would really appreciate some more input.

Around the time I started this job and met this girl there, I met and started going on dates with another girl. Let’s call her Jane. I hadn’t made any sort of commitment to her as I tend to move quickly in the situations and was trying to do something new by slowing down and not jumping into things. I like Jane. She’s sweet and looking for the same things long term as me. She is very into me. Constantly telling me how smart and handsome she thinks I am. We have a good time together. Lately I’ve been feeling awful when I see her because I’m constantly thinking about this girl at work when I’m with her. It’s really starting to bother me and making me feel incredibly guilty. Yesterday for example Jane got in touch during the day and asked if I wanted to get dinner in the evening. I hemmed and hawed all day via text about working latel possibly, all because the day before work girl said we should get a drink this week and I didn’t want to double book and blow it if she finally asked me out (which is a whole other issue April, I’ve been doing my best to play it cool with work girl, and every time I do she’s going way out of her way to interact with me and do “our” little thing but when I try to take that to next level by suggesting we do something after work I’m getting the absolute lamest excuses.) finally when the whole day went by and me and work girl hadn’t said a word to each other, and she left for the day, I told Jane yes let’s have dinner. And when she wanted to wait for me in the lobby of my building I got worried someone else would see us and it would somehow get back to work girl (which I realize now might actually be a good thing). So we go out and it is a gorgeous evening in nyc. We go to a place Jane really likes in Hell’s Kitchen and the first thing I can think of is how much I want to bring work girl here. Later when we’re walking all I see while Jane is next to me is places I wanna take her. Makes me feel pretty awful I’ve had this same issue during some intimate moments with Jane where my mind literally goes to this other girl when I’m meant to be totally in the moment. I can’t help it.
I don’t know exactly what my question is. It just seems crazy that I’m letting someone I’ve yet to go on a date with, and very possibly won’t ever, kind of ruin something I have with someone else. Literally the only complaint I have about Jane is that she’s not work girl, as stupid as that sounds. She is beautiful and everything I look for in a woman. I understand part of this is the wanting what we can’t have thing and that’s definitely true but wanting someone else and letting them have this much power when there’s nothing going on is pretty crazy.
On the work girl front like I said. I’m doing my best to only interact with her when I would with any other coworker. And sure enough every time she makes until about 2pm before coming over chatting me up and trying to get lunch or coffee with me. So I say to myself great it worked! And try to turn that into hanging out with her, and then I get the worst excuses that make me feel kind of insulted to get. Anyway, that’s what’s going on, please help.

[Dom1]

That’s all very put and probably very accurate. I find it really difficult to project the image you write about and I don’t really know why. I reasonably good looking. In decent shape. I’m well educated. Well read. Generally have good taste. Pretty successful in my career at this point. I don’t know…it’s very hard to channel patience and “coolness” toward this situation when everything else I’ve gotten in life I got from being proactive…

[Dom1]

Yeah I do see that. And I’ll admit I’ve been guilty of the same at times. What I don’t get it is why a guy who is being genuine and, frankly, pretty charming, and doing a bit of courting is less appealing to a girl than one who (from her perspective I guess) is acting distant and disinterested. I mean I get it but I don’t. It seems like a game that this girl probably is unaware that she’s even playing. I didn’t text her yesterday by the way. I’ll hold off like you said until I can see her in person.

[Dom1]

So April. I continued taking your advice this week. I went the first few days of the week basically ignoring her. No texts or messages and didn’t say more than good morning once for like 3 days. All of a sudden on Thursday it seemed like something changed. First thing in the morning she texts me asking me if she bring me in coffee on her way in (it’s amazing how much interaction with this girl at work is centered around coffee). Anyway, maybe I’m thinking crazy but it’s like just a few days of pretty much ignoring her existence made her do nearly a 180. She talked to me all day, asked ME to go for our usual afternoon smoke, and then we both worked super late. It was Saint Patrick’s in nyc and most of our office was drinking by 8pm. I asked her if she wanted to go for a drink when we got done. She agreed. Things got a bit bungled when another coworker came back into the office drunk around 10pm and demanded we go join her for a drink. My girl wanted to back out which I wouldn’t let her do because really did not want to go anywhere alone with the other girl in the state she was in. So the three of us went out on the most obnoxious night of the year. Before we even got to the bar I told her this was pretty much the opposite of what I had in mind for our drink to which she said we’d have to have a rain check on that. We had an alright time out. We ended up alone back in front of our office building later waiting for the car service and agreed again that we’d try again soon for “our drink”. Later that night I did something a tad foolish. When I got home I texted her and told her how beautiful she looked today and that even though it’s not what I had in mind I had a great time. She said I was sweet to say so and she had a good time too despite the circumstances. Then yesterday same thing, coming over to ask me questions she could ask anyone, namely our boss, inviting me out for coffee and something sweet later in the day to help us power through the awful project were both working on. Our boss told us we could work late again but didn’t have to. We could start fresh on Monday is we wanted. We both agreed we weren’t staying past 7. Then she let me know she was leaving and looked like she was waiting for me to ask her to do something. Which I didn’t. I don’t know I don’t think I’m crazy. She had a good time with me on Thursday, I had her laughing and smiling all day and night, and all of a sudden she seems really receptive. Is it really that simple as playing it cool for three days? Maybe something about her situation changed but I’m kinda scared to ask about that.
So now I want to ask her out for tomorrow evening. Something in between the friend thing and the date I want, a comedy show which I mentioned to her before and said she’s been there and likes it. April I know you told me to ask in person and I get why, texting becomes the primary way people communicate and that’s not necessarily a good thing. But I have no cause to see her before Monday and limited opportunities to ask even then. I’ve never called her. I feel like with texting these days actually calling someone and making them pick up the phone is like some intimate thing reserved for people who are involved with each other in some way. So what do I do now? I’d love to generally hear your thoughts. Thanks April…

[Dom1]

As usual I don’t know what I’m supposed to do with this. First she’s saying don’t wait around for her situation to change and 8 seconds later she’s saying we could wait until it does. I’m suspecting what I was last week, that I’m very politely being told to fuck off. Nothing has changed about how attracted I am to her or how much I feel like I wanna date her but I feel like I way overestimated her interest level from the start. Now the word “friends” is being used. If she was ever as interested as I thought she was its taken a sharp decline probably due to how poorly I handled this whole thing. I feel like telling her I have no interest in being her fucking friend! I’ve got enough friends. But at the same time I can’t resist the idea of her and I spending time alone, as much as I know it will probably serve no other purpose than to further frustrate me. See April I definitely do know better but I just don’t act like I do. You’d think I was 18 or something and new to how all this works, but I’m 32 and still don’t get it.

[Dom1]

So the response I got was to my message on ssaturday was not until about 24 hours later on Sunday around the time I proposed to meet. She was visiting her parents and had plans for dinner with them. Fine. She suggested a museum I check out. Fine. I tell her she should come with me, and that obviously I do t know when to quit. I’m really beating a dead horse at this point. No response at all until another 24 hours or so later today when we’re at work and I ask her if she’s going out for coffee. I get the messages below:

[Dom1]

So I took your advice even though it is pretty much the opposite of what I expected you to say. I texted and told her I was sorry for being confusing the other night and how about letting me redeem myself? Named the place we were gonna go the other night for a walk and said tomorrow (she already said no to dinner so that seemed like pushing it). I honestly don’t think this is gonna work. I have a feeling she’s gonna say now that I’m a nice guy but with her situation it’s not a good idea. Which is why is was going to just let it go for the time being. I feel like now it’s becoming a thing and I have zero power and she’s just not gonna go for it. BUT I’m hoping I’m wrong. You’re an expert for a reason and I definitely don’t know what I’m doing here…
She seems to take forever to respond to texts so who knows when I’ll hear back from but I guess I’ll let you know. Keep your fingers crossed for me April.

[Dom1]

So I posted all of this the other night but apparently it didn’t work. So this is what happened:
On Thursday I didn’t talk to her much. When I did I didn’t mention hanging out. She messaged me in the afternoon asking to go out for coffee and a smoke. Which we did. I still didn’t mention hanging out. She asked me if I was still going and I said yes. She said her plans with her friend were still up in the air but she might be joining me. I let her know what time I planned on leaving.
When that time came I went to her desk and she said she was just gonna go home, not even see her friend. It had been a shitty day and she was tired. I didn’t know what to say that. I’m thinking if she didn’t want to hang out with me she already had her excuse lined up with her friend and I would never know the difference. So I left and immediately texted her because I didn’t want to have a whole long conversation in front of people. Told her I was around the corner meeting my brother and that she should at least come take a little walk. She said ok and she was leaving in a few mins. Somehow in our next few messages apparently she misunderstood me, thinking I had made plans with my bro instead of just meeting him to give him keys and she got on the subway and left and left me sitting there waiting for her. I still don’t really get where she got that from. So needless to say I got a little annoyed and more than a little hurt and upset. I texted her asking if I was politely being asked to take a hike. In which case I would do so. She responded saying her situation hasn’t changed and that our miscommunication was definitely my fault. Which I still don’t really agree with. I was basically crushed again. I’m amazed at how crushed I was sitting there by the subway waiting for her and finding out she was already gone. I don’t understand why she seems interested in hanging out with me in the abstract but when it comes down to doing it it’s a different story.
I was honestly so upset that night. I felt really stupid and really worthless. I deleted her number then and there knowing myself and knowing otherwise I would keep trying what I’m trying and keep getting hurt. She responded to my last message yesterday morning, early, explaining why she thought we weren’t hanging out and left. She said her thought process was logical. I told her that it was adjacent to logic and that it was fine. I was really dreading going to work yesterday because even though no one else knew I’m unbelievably embarrassed. I don’t know that I have ever read a situation this badly. It’s been many years since I felt like this.
I didn’t speak a word to her all day. I didn’t even want to give her the satisfaction of catching me looking at her, though in pretty sure I caught her once or twice. Our team even had a meeting in a small conference room and I still didn’t so much as acknowledge her. I know that’s not exactly what it means to play it cool but it was the best I could manage. Thursday night serious hurt and it probably shows by me ignoring her but I guess I also wanted to see if she came and talked to me or asked me for coffee like normal, but she didn’t.
I feel like a real fool April. Mostly because I’m still incredibly drawn to her. She looked gorgeous yesterday and it was not easy to go even one day without talking to her. I’m not the kind of person who just gives up on these things and I know that ignoring her makes me seem petty and hurt. I regret texting her the thing about taking a hike out of being hurt. But I don’t know what else to do. It seems better than continuing to follow her around like a pathetic puppy dog.

[Dom1]

So I took your advice and texted her that tomorrow I was going after work and that I hope she wants to join me (she specifically told me she was joking about that reverse psych thing). She responded later saying she has tentative plans with her friend she hasn’t seen in a long time (she mentioned the friend by name) but otherwise is totally down, and If she ends up seeing her friend tomorrow there will be many more spring days for us to explore. So I don’t know. If it doesn’t work out tomorrow I’m guessing that would mean if I want to try again I have to ask again which I’m not super keen on doing a third time. I don’t see her asking me. She is pretty passive and quiet and I just don’t see her making a move even if the ball is clearly in her court. I don’t want to give up on it but I guess I’ve put it out there and there isn’t much else to do about it….I guess I’ll find out tomorrow. “Totally down” is a much better response than the one I got when I asked to go to dinner, so maybe the non date thing will work out better. I don’t know…I think if she doesn’t come tomorrow I might be done with this. I do really like her but I don’t see much else to do…I feel like timing works and things just click with people or it doesn’t and even if there is attraction and chemistry things die on the table.

[Author]

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