“Please Help Me Decipher These Mixed Signals”

I’m a man in need of advice and a woman’s perspective. “Nadine” and I used to work together and had some sort of “connection,” so one night during a Whatsapp chat I suggested going for a drink, and she gave some vague response that I took as her way of letting me down gently. So I said something like “No worries, wouldn’t want anything to get awkward between us at work,” and it was never mentioned between us again and things at work were normal as usual. (By the way, I wasn’t her boss, and I am in the UK where workplace relationships aren’t frowned upon as they seem to be in the US.)

I left not long after (nothing to do with her). We kept in contact via WhatsApp, but it was always me that initiated contact, usually by sending a silly meme, which led to the usual “How you been?” type of conversation. I often got the feeling she only replied to be polite, although often it led to lengthy chats, and in May she contacted me about jobs where I work as she was looking for a new one.

I’d often suggest that we should meet up for a coffee and her answer was always “sounds good,” which I imagined was her just being polite and that, should I ever actually ask, she’d just make an excuse to not meet. However, this week I messaged her (first time since May) and said I’d be over near her neighborhood and did she want to meet for a coffee, and she answered literally straight away saying, “What time?”.

So we finally met up again after more than four years of nothing but WhatsApp chats. I played it casual and was dressed in just jeans and a t-shirt and trainers (sneakers, if you’re American), and when she arrived, it looked as though she’d done her hair and make-up and “made an effort,” if you know what I mean. We caught up and had a good chat for about 90 minutes and covered everything. It went really well! We parted with a peck on the cheek and I said we shouldn’t leave it another four years before meeting again!

I know for a fact she’s still single and I suggested next time meeting up for a drink, but she said something about getting some of our other old colleagues out, too. What confuses me is she obviously knows I like her in a more than a friend type of way, so why would she think about applying for a job where I work and meet up for a coffee with me if she doesn’t feel the same way?

Should I wait a few weeks and next time we chat ask her out for a drink one night? I’ve decided that the next time we meet, I’ll ask her out properly and will explain that I know she doesn’t feel the same way but that the offer is always there if she ever changes her mind. And I’ll tell her exactly how I feel about her (I’m guessing in person is better than via WhatsApp!) and if that means it’s the last time we ever have anything to do with each other, then I’ll have to accept it and move on.

I’m really confused by the signals, so any help from a woman’s perspective is greatly appreciated. – Confused By Mixed Signals

You’re making things a lot more complicated than they need to be. Instead of trying to guess what Nadine is thinking and feeling – not to mention telling her that you know how she feels when you clearly don’t! – why don’t YOU start being more direct? Look how well it worked with the coffee date. Whenever you suggested getting coffee “some time,” Nadine’s response was “sounds good,” but the one time you were direct and gave a specific time, she responded enthusiastically. Let this guide your next interaction with her.

If you have such strong feelings for her that you are still kind of pining away years after even seeing her, why would your response to a great coffee date be weeks of silence and then a vague invite to have a drink some night? Women tend to like men with confidence, so show her you have some by reaching out NOW and telling her that you really enjoyed seeing her, that she looked great, and that you were wondering if she would like to go out on a proper date. Don’t make it a drink date. Make it a dinner date. Name a specific day and choose a restaurant not too far from her. Tell her you heard they have good whatever – if you can remember something specific that she likes and there’s a restaurant that does that item well, even better! – and ask if she’d like to join you for a bite. Use the word “date” – “Would you like to go on a date with me?”. It might feel scary, but you can do it!

The more direct YOU are, the more direct Nadine will have to be. Use the word “date,” and she’ll understand what that means. You have assumed that all along Nadine understands that your invitation for “coffee some time” or “a drink some time” is romantic in nature, but maybe she doesn’t. Maybe she thinks YOU are giving mixed signals. Or maybe she understands your interest but isn’t interested back and can avoid hurting your feelings by matching the vagueness you always present. Be direct and limit that option for her. Ask her out on a proper date that she has to say “yes” or “no” to. Her response may hurt your feelings, but I think that would be preferable to this uncertainty you’ve felt all these years.

What I would 100% not do if I were you is tell her that you know she doesn’t feel the same way but the offer is always there if she changes her mind. Look, that sounds pitiful. You DON’T know how she feels, but if you learn that your feelings aren’t reciprocated, why should your offer “always be there for her if she changes her mind?” It shouldn’t be! You should move the hell on if you ask her on a proper date and she says no. It’s been years now, and maybe you find comfort in this weird grey area where there’s always a maybe-potential something that could happen. But you do yourself no favors staying in that area. You aren’t moving forward – not with Nadine and not on your own. It’s time to move forward! And if it’s not to be with Nadine, then moving ON is also a forward movement.

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If you have a relationship/dating question I can help answer, you can send me your letters at [email protected].

37 Comments

  1. LisforLeslie says:

    I interpreted this completely and totally differently.

    Why did she apply for a job where you work? Why does anyone move to a new job? More pay, more responsibilities, more alignment with career goals. She’s not looking for a new job because she wants to be with you.

    Why did she meet you for coffee? She’s looking for a new job where you work and thinks you could give her some insights and put in a good word. How much of the conversation was about work, the work you’re doing, the work she wants to do…. blah blah blah.

    Why did she go all out on getting ready? Because she wants to look her best because she’s looking for a new job.

    Dude, my dude, she knows you have feelings for you. She is using them for her own purposes. I don’t think she’s taking advantage of you here, but I also don’t think her motives are truly on the up and up here.

    She’s not into you.

    1. Yes, and all the more reason to force her hand, so to speak, by being direct and asking her out on a date. The LW needs to move on and I think any guessing to her motives leaves the door open to continue pining away and periodically reaching out. Best just to ask a direct question and move on if not given a direct answer.

    2. Bess Marvin says:

      That’s so interesting — I thought the opposite, like, why would she continue to chat with someone for FOUR YEARS if she wasn’t at all interested in him? I would not have “lengthy chats” for years with a former coworker who meant nothing to me.

      I agree that her asking about jobs where he works is probably not related to romantic interest. I do have casual acquaintances with whom I text only occasionally, so my thought was maybe that’s what he is to her.

      Anyway, LW, for sure follow Wendy’s advice. If she doesn’t know you’re interested, you’ll have to do more than hint about it.

    3. Anonymous says:

      She’s not looking for a new job, she never went through applying at my place as the hours didn’t fit in with her youngest kids school times, plus she’s still at our old place, has been promoted to Team Leader and said she really enjoys the job.

      1. I think the fact that she brought up co-workers when you asked about a drink indicates she wants to keep it friendly/maintain her network. I’m pretty sure she understood you meant a date. I would have coffee with an old colleague and not consider it a date, but a drink is different. The only way to know for 100% certain is to ask her specifically on a 1:1 date, but I think she likes you as a friend.

  2. Anonymous says:

    Thanks’ for everyone’s input on here.

    After going round in emotional circles I’ve decided that when we next speak, whether that be in person or via Whats app, I’m simply going to ask her out one more time and when I get the inevitable ‘thanks but no thanks/ I don’t view you that way’ etc etc I ‘ll just say I understand and that’s fine but if she ever changes her mind the offers always there I think I know her at least well enough she won’t mind that).

    I’m not going to bear my heart and soul to her that I may have once planned to do as there would be no point if she says no, so then the balls in her court and if I never hear back from her again then so be it .At least I’ve been true to myself and her

    . I’ve based this on the old saying of ‘The biggest regret of your life won’t be what you did, it’ll be what you didn’t do’

    1. That’s the way to go! I would reach out in the next few days instead of waiting until the next time she reaches out. Be assertive and get and answer and move on, whether it’s knowing she’s not into you or that she’s interested enough to have a date with you.

      1. Anonymous says:

        Thanks for the reply Wendy.

        I now know I’ve been dwelling on this for far too long, especially when it came to asking her out for even a coffee, mainly due to lack of confidence on my part, as I didn’t expect her to say yes, and in hindsight as well as the many ‘sounds good’ , there was one ‘I’m really busy at weekends, what with running round after the kids etc’ so think in the back of my head that may have been subconsciously stopping me from asking, however when I did it went like this: 7.55pm ‘Alright Nadine, I’m over your way Saturday, fancy grabbing a coffee’.7.56 ‘Hey I’m good thanks and you? What time you over?’. So you can see how the swiftness of her reply plus the enthusiasm added to my confusion!!
        Anyhow I’m going to contact her next weekend vis WhatsApp again, as that’s nearly always how we communicate and what will be will be.
        It will only have been 2 weeks since we met, but can’t do it this weekend as I’ve a lot going on and need to be in the right frame of mind.

  3. Manifestation Station Girl says:

    From a woman’s perspective, this is painful to read. If she does like the LW (or did at some point) it’s been 4 years?? I’ve been on the receiving end of this. I actually liked the man (a lot). He moved at a glacial speed and although we went out on a few dates, it was way too slow for me. I moved on. Why is LW so timid? You’ve got one life to live, LW. My advice to you would be to get in the game. Not tomorrow or next week but ask her out today. Get an invite on the books. If she doesn’t respond enthusiastically or counteroffer for another time and place, then move along. Life is too freaking short for this. Good luck.💗

  4. She’s just networking for a new job. There are no mixed messages. Some women (myself included) go on all social outings wearing makeup and dressed decent; that doesn’t mean she’s trying to impress you.

    1. Anonymous says:

      She’s not after a job, she never applied for the one at my place as it didn’t fit in with her kids school, plus she’s since been promoted at where we used to work and said she really likes her job there.

  5. The thing is, right now you’re in “Heisenberg’s Dating Uncertainty” state. You won’t ever know for sure unless you open the box… Make the move! Here’s what I would say: “Hey, I’d like to take you out on a proper date. I’m thinking [name of restaurant] next Thursday at 7:00. Sound good?” That’s all you need to say. If she says no, don’t get upset, don’t act hurt, don’t act embarrassed, don’t act any differently, just let it roll off you like water off a duck’s back, and go back to friendship as usual with her. The thing is, approaching her with directness and confidence may be enough to tip her interest in your favor, it might just give her enough to at least be curious whether there might be something worth exploring with you… Confidence is very attractive, and she may have never seen that quality in you.

  6. Anonymous says:

    I find the whole thing a bit odd on his part. For 4 years she’s been saying “no, thank you”. There are no intermittent dates to give mixed messages. She is saying, very clearly, “no”. After 4 years of being told ‘no, thank you’…why isn’t he listening? She contacted him when she was considering working in his company. The fact that she later decided against it doesn’t negate that. She was clearly serious about her job search since she found out the hours, weighed them against her personal life. The advice to ask her for a real date…place, date, time, activity…is good. But if she says “no, thank you”, then move on. Her ‘no’ means ‘no’.

  7. Katya Gardner says:

    Wow. Jonathan, did you really see the need to repeat Wendy’s advice word for word, practically? She is the advice columnist. The letter writer could have written to a male advice columnist if he really needed that imprimatur.

  8. Anonymous says:

    I didn’t realize men’s comments weren’t welcome here. /s Seems like that’s up for Wendy to decide how she moderates her site…

  9. Concerned dude advocating for the lady says:

    I empathize with your uncertainty – we’ve all been there – but I just wanted to point out one thing that bothered me.

    “What confuses me is she obviously knows I like her in a more than a friend type of way, so why would she think about applying for a job where I work and meet up for a coffee with me if she doesn’t feel the same way?”

    I would caution you against thinking that your position precludes her from seeking a job whether she likes you or not. Maybe in a very small company where you would be working side by side, but normally work is work – best to leave your romantic feelings out of it.

    I doubt she reached out after four years using work as an excuse without being legitimately interested in the company, which she has every right to be.

  10. LisforLeslie says:

    You sound like a thoughtful and considerate person and I hope that putting yourself out there (which can be nerve wracking) is successful. If anything, just having an answer may bring some peace.

    Good luck dude. I truly mean it.

  11. Bonnie Baselt says:

    I agree with Manifestation Station – ask her now even if it’s for a date in the future; she may need to arrange childcare. It’s a waste of time to try to figure out what she’s thinking – only she has the answer to that. Or maybe she doesn’t either!
    Tell her you enjoyed your time together over coffee and you’d like to invite her out to dinner (on a specific day) – as your guest. If she says she’s busy, ask her what day would work. If she still puts it off, playfully come back with, “Well, you’ll need to ask me next time!” Then the ball is in YOUR court because you can decide if you want to continue your online friendship.
    And, PLEASE, tell everyone what happens – you have a lot of people invested in this!

  12. Anonymous says:

    Ok for the last time, she’s not interested in a job!!!!!!
    The vacancy at my place was 5 months ago and she’s still at the place we worked, has been promoted and says she likes her job there.
    I know most people on her are American and you’re all obsessed about the job thing!
    In the civilised world we don’t obsess about work as much as you lot, mainly due to the fact we don’t have to rely on our employers insurance to make sure we don’t die due to not been able to afford and access healthcare.

      1. Anonymous says:

        Hi Wendy
        It went kinda how I guessed it would.
        Messaged her late Friday night and after a bit of general chat about work, how time had flown by etc it went like this:
        It was really nice catching up the other week. You’ve not changed a bit, still as lovely as ever.
        Yes it’s been a long time, didn’t realise how long. Oh I’ve got older lol.
        Nah you’ve not
        We’ll have to meet up again.
        Yes will do.
        What about going out properly one night for a drink and bite to eat?

        This was then met with a long silence until she replied about 12 hours later next morning with:
        I don’t have time to go out lol.
        I kinda knew she was the sort of person who’d try to let me down gently so I replied:

        I’m sure you do lol

        To be honest I’ve always liked you ever since we worked together. I think you’re stunningly pretty and a really lovely person who I’d love to get to know better so if you should change your mind the offers always there.

        That was 24 hours ago and she’s not replied and I very much doubt she will, as I’ll probably never hear from her again.

        If she should reply I want to tell that I realised when meeting her how quickly time flies bye and that life’s far to short to not be honest with people and also how someone as lovely as her shouldn’t be on her own and deserves a guy that’ll treat her(and her kids) how she deserves to be treated and when it happens I hope he realises how lucky he is (I genuinely mean this) .

        I may have gone about this all the wrong way, I don’t know, nor do I care as I I’ve finally told her what I think about her, and won’t spend the rest of my life thinking ‘What if?’

        What will be will be, and sure I’m going to be sad for a while but I’m glad I’ve finally got it off my chest and eventually will move on no matter how long it takes.
        Thanks for the advice.

  13. Anonymous says:

    Further to what I just wrote, it’s now been over 2 days since I last messaged her and to be honest I’d rather she’d said thanks, but no thanks/you’re not my type/it’ll never happen etc etc than just leave me hanging. I know this was one of the outcomes that could happen but it feels like I don’t have real closure.
    I was thinking about leaving it week or two and then just saying something like :

    Hi Nadine, sorry if it weirded you out ( maybe I’ll say made you feel a bit awkward?) when I asked you out, but when we met I realised how time flies by so quickly these days that life’s too short not to be honest with people.
    And no I’m not still harbouring a thought that I still stand a chance as I know I don’t, it’s just like I need to close this whole chapter properly and fell like I haven’t.

    1. You have closure! You don’t need her to say ‘no thanks’ or anything more. She told you she didn’t have time to go out. THAT means ‘no thanks.’ Now you know, and you can move on!

      1. Yes 100% don’t do that. You do have closure. She said no and she said it nicely. To reach out again is impolite. It’s okay to ask someone out once, and then you need to respect the outcome.

        And ok, let’s say you did send exactly that message. How would you like her to respond? “No worries?” “I understand?” “All the best?” How does that give you closure, or what does that do for you emotionally that you don’t have right now? Do you want to still be friends? Then you need to craft a very different message. Do you want her to say, no, wait, you’ve got it wrong, you do stand a chance? That’s not going to happen. If she should reflect upon your message from 2 days ago and decide she’d like to go on a date after all, she knows how to reach you.

        The message as worded above comes off pushy and not taking no for an answer At worst, or needing validation at best.

  14. I left a comment above saying I think she just wants to be friendly, without realizing this was already resolved.

    Reading the original post again, she would say “sounds good” to coffee, but she didn’t give you an answer the first time you suggested a drink, and the second time you suggested a drink she said “with other people.” I imagine she went for coffee because she was free when you asked, thought it would be low-stakes, friendly, you two could catch up, and that would be that. To me, and probably to her too, coffee isn’t a date, it’s a thing friends or colleagues do, it’s within business bounds. She never said “sounds good” to a drink because she knows that’s going into territory that looks like a date.

    She was trying to be nice, and if you needed her to unequivocally say no to a date, then mission accomplished, so that’s good. But reading this, as a woman, it was clear to me she was being friendly only. I think it would be good if people picked up on these kinds of cues sooner, or just cut to the chase and asked for a date sooner.

    1. Another observation here, and sorry for the multiple posts, is that she had said previously that she’s busy at weekends. That, like saying “sounds good” to coffee but not a drink, is a way to set a boundary without having to be direct and say she’s not interested. It was a polite no, and then she said it again a little more directly when you asked her again. Do you need her to say the words “no, thank you, I am not interested in a date?” Women have been conditioned not to do that. They instead say “I have a boyfriend” or “I’m too busy to date,” because some men will get rude and angry when women are direct with them. You got a polite refusal, and that’s the conclusion of the matter.

  15. LisforLeslie says:

    I think life and dating is too complicated to get stuck in the “should haves”. You should have done this, she should have known this, you both should have said this. Too hard.

    Going forward when someone is interested, truly interested, they will find a way to reach out and keep communication flowing, not press an interminable pause button. I also think Kate is right, in the future, if you know someone is single, and you want to date them tell them up front, within a couple of weeks. I know it’s hard being a guy, I don’t want to diminish the pressure, but too often women think they made a new friend and it’s really disappointing to find out that the entire time the friendship wasn’t the goal, it was a stepping stone. And if you can set aside your dating goal and truly be friends, tell them, but also be really clear with yourself that dating that person is off the table. If you get the sense that a person is playing games, that they pull you in just to keep you on the back burner – you don’t need that crap. Walk away.

    In this case, silence is an answer. It’s not the answer you wanted, but it is an answer.

  16. Anonymous says:

    The reason I feel the need to apologize if asking her out was awkward is because although we haven’t worked together for over 4 years we’re both employed in the care sector in the same county for an organisation made up of several charities working together and there’s often events when they all meet up and I’d rather have gotten things sorted properly now even via WhatsApp, just in case I should bump in to her at one of these, (especially as she’s been promoted there’s more of a chance) so there’s not that embarrassing awkwardness should this ever happen.

    1. Oh, no, you don’t need to apologize for asking her out. There was nothing wrong with that. Any additional reach out is going to make her feel awkward though. It will make her feel like she has to reassure you. Or make her feel called out for politely ghosting you. It’s not the right thing to do. If you gracefully let this go, it sets you up better for if you do run into her again. Trust me.

  17. LisforLeslie says:

    Nope, it’s unnecessary and you’re putting (unintentionally) the onus on her to say it’s all ok. Just let it go, when you see her next, greet her with a friendly smile, shake her hand and say “it’s good to see you, I hope things are going well, let me know if you ever want to catch up over coffee.” which says “balls in your court, I’m around if you want to chat, but I’m not pursuing you, have a nice day”

  18. HeartsMum says:

    Please, take on board the kind and valuable advice you’ve been given. In one response, you said something like, “I’ve done it all wrong”. No! If you’re following the guidance here, you will get it right eventually. She was not the right person, that’s all.Redirect your efforts elsewhere (and really, avoid work colleagues).

  19. LisforLeslie says:

    Don’t apologize, it will make things more awkward. When you see her just greet her with a smile, shake her hand hello (no weird side hugs) and say something noncommittal like “it’s great seeing you” and do the chit chat and if you feel like it you can say “If you’re ever interested in catching up over a cup of coffee, give me a call” – it puts the ball in her court but says “I get it, we’re never going to date, coffee is for friends and that’s all we are”

    Sorry it didn’t work out but at least you have answers right?

  20. I’m very proud of you for putting yourself out there- it can make you feel very vulnerable, but playing it safe all the time doesn’t allow you to really enjoy life. I hope you can look at this as a first step in opening yourself up to new possibilities; it gets easier with practice!

  21. Anonymous says:

    So her reply to me apologizing if asking her out made things awkward was ‘Hey. Don’t worry’,

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