[Dom1]

Dear April,
I could really use some help because I am at a loss!
A little background: I’m a guy, 32. Soon to be a lawyer. She is 30, soon to be the same. We started at a new job on the same day about 2 months ago. I was attracted to her immediately but was honestly a little intimidated by her and by the new job environment to really flirt or be myself around her at first. That changed pretty quickly. We ended up spending a good deal of time together alone and there was definitely chemistry. I noticed her looking at me in “that way”. You know what I mean. Holding eye contact for extended moments and she would have this enormous smile on her face when we’d see each other in the morning. I was becoming more and more drawn to her really fast.

The situation arose over the past few weeks. Our team went on a happy hour outing after work and we were joined at the hip the whole time. So much so that I didn’t want people to start whispering about us. Office gossip can be a problem. So she was taking a week off the following week to take the bar exam. That Friday I bought her a book and a nice card and left it at her desk. She seemed to really like that. We went out for lunch alone that day and I swear the chemistry was ridiculous. I told her at the end of lunch that she should get her answer ready,because when she came back to work after the exam I was going to ask her out. I got that enormous smile again.

So the week passed and she came back this week. I let Monday pass and emailed her Tuesday to go out to lunch again. She texted me back instead of emailing, giving me her number. Clear signal right? So at lunch I gather up the courage to ask her and I do. I say “you should let me take you out to dinner”. Huge smile. “I should huh?” “Yes I think you should “. Then this: “well, I’m kind of in a ‘it’s complicated’ situation right now so…” I was speechless. I had specifically asked when Valentine’s Day was coming up and her birthday what she had planned. She knew I was asking if she had a boyfriend. And her answer to both was having dinner with her sister.

So I don’t know what to say. I really didn’t see that coming and am at a loss for words. I try to wrap up our lunch and get away from her because I feel totally awkward and embarrassed and honestly have no idea what to say now. I manage to ask her if I was just totally in left field with asking her, to which she says no that was probably her fault.

So here’s the problem. I know this girl likes me. And I really like her. I know she purposely never mentioned a significant other in front of me because she could tell I liked her and didn’t want me to know. I’m no stud and I’m not arrogant, but I know when a girl is interested and when she’s not. And this one is. At least enough that she entertained the idea of going out with me. The issue is what I do now. Everyone is telling me to basically ignore her at work. No more lunch dates or getting coffee. Just pretend she’s not there more or less. Which is totally not what comes naturally to me, playing it cool like that. I want to let her get to know me more, let me make her laugh some more, and hopefully she’ll decide she wants to go out with me. I know from experience that this a super delicate moment and if I have any shot with her at all I could ruin it really fast by handling this the wrong way. I got lucky in a way that next day after this I got a terrible flu and went home early and missed work Thursday and today. I honestly think I was so crushed by her response I was worn down and ended up getting sick. I really was totally crushed that afternoon. I barely remembered what that feeling was until now. I haven’t felt it years. Rejection is fine, but this was different for some reason.

So what do I do? Play it cool? Or keep being the charming genuine guy I am and don’t give up? Thanks a lot for reading all of this. I would love your advice!

[April Masini]

All I heard her say that it was complicated. I didn’t hear her say she had a boyfriend. If the situation arises again, you can ask her what she means by it being complicated. It’s a fair question. Either way, she definitely likes you and she’s game, but I think you need to find out a little more before you get emotionally committed. Take her out for drinks and get to know her a little better. This isn’t that full on romantic dinner and a movie date — it’s an exploratory date. You can invite her to go for a walk, or play tennis — something that’s fun, but that’s also an opportunity to talk to her more and learn if she’s someone you still want to date or compete for. It’s not over. You just need more information. 😉

Hope that helps!

[Dom1]

Thanks so much April! Believe it or not last night after I posted my question I did just that. I texted her asking do something after work this week. We’re in New York City and the weather is gorgeous so I asked her to take a walk on the high line. And that it would not be a date. She responded later after I was already asleep saying it sounded enticing but also that maybe I was using some kind of reverse psychology to get her on this “non date” though she might have been joking. It’s been busy at work today so I haven’t talked to her to know what her answer is. I hope she comes. I never know when you are supposed to take a polite no as an answer and when maybe some persistence is charming and might pay off. It’s very hard to tell. I had another conversation with her after asking her out and she said she is currently a very “confused girl” whatever that means. If she doesn’t say yes to just taking a stroll and talking in guessing I’m about out of moves here right?

[April Masini]

I think there’s more to this story! She’s throwing up a lot of smoke bombs so you can’t see the real her. Instead of going along, why not take the lead? Tell her that there was no reverse psychology involved at all — it’s not your style. Just wanted to spend some time with her and see where things go. Then ask her if she’s in or out, and give her a time and place. At a certain point you have to take control of the dynamic here because a) you’re the guy doing the asking and b) she’s playing games and you need to know if she’s flirty or avoiding letting you know some bombshell (like she’s married with six children). Some people thrive on this type of teasing and flirting because it gives them attention and a sense of control, and you need to know if she’s into you, or just the attention and control she’s getting. Your move. 😉

[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.

[April Masini]

If she doesn’t show up tomorrow, then I agree that you should move on. But don’t forget about her — just don’t keep her on the front burner. Many times women will find you more attractive when you’re unavailable. 😉 Nice guys finish last, so maybe it’s time to stop being so nice and start being the guy SHE can’t have. You know how people want what they can’t have….? 😎

[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.

[April Masini]

I misunderstood you, too. When I read what you wrote, I thought you meant you were meeting your brother, as in “for drinks” or “for dinner”. And I was thinking to myself, why did he tell her that? That doesn’t sound like he really wants to see her! It definitely wasn’t clear to me that you were meeting your brother to give him keys and then to separate from him. I would have done what she did! It definitely was a misunderstanding, and she wasn’t wrong.

My advice is to apologize and tell her you want a do-over. Tell her that you owe her dinner after all the misunderstanding that you agree on further thought, was your mistake. Take the pie in the face and show her how gracefully you can admit your mistake. Even if you don’t believe it was your mistake, don’t fight with her when you want her! 😎 Tell her Saturday night, 7:30 p.m. at (pick the restaurant). Tell her it’s your treat — and you want to make it up to her. Drinks, dinner and fun.

This might get you out of the bad groove you’ve gotten into with her. 😉

[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.

[April Masini]

What’s the worst thing that can happen? Right. Rejection. And nobody ever died from rejection. And besides — the upside is large if she says yes!

Next time — ask her in person. Texting distances you from each other and there’s more likely miscommunication with texts. Besides, women like the sound of mens’ voices. So, next time…. 😉

[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]

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.

[April Masini]

I think you should move on. You’re right — you don’t need to friend zoned. Next! 😉

[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…

[April Masini]

What’s the rush? Wait and ask her in person. 😉 She likes you better when you’re not so available — as you can see! 😎

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