Nice, flirty, interested; how do you tell?

Hi Guys,

I have wondered about the question above, since I’ve been divorced for six years.  There is a man that has been coming into my work center for a few years now. We engage in the normal pleasantries and for the past six months he has been very
attentive to me. He lives in another state. We don’t talk long, as he has to prep his work area down the hall, then leaves on a flight.

He always comes to my area, smiles, jokes around and asks what my plans are for the weekend; the next week he asks if I did the activity I planned. He says some really sweet things like it made his week to see his favorite agent, or it wouldn’t be worth coming here if I wasn’t there. He is not afraid to be vocal when he says these things. A lot of people won’t give me the time of day due to my profession, but he isn’t afraid of speaking or being seen with me.

I don’t know if he’s married, no ring, but that doesn’t mean anything. I am very shy and am not good at flirting but I tell him how nice he looks etc. We just click and I think I have a bit of a crush on him. I was thinking of writing a short note to tell him how much I admire him and the aforementioned qualities. I don’t want to hurt our passing friendship, so I won’t say how I feel when I see him. I really don’t know what to do and I don’t want to read anything into it but that he just like teasing me, for fun.

What do you think I should do? Should I let him know by note that he’s a wonderful person or is that going to make him
uncomfortable?  I don’t ever want to do that. How do you tell? It seems like such a fine line.


Dear Ann,

Thanks for your question. Now you got us curious. What do you do for work? (Can you even tell us?) Why would people not talk to you because of it? (And it’s a good sign that he does.)

You are so right when you say this is a fine line. It always is. The fact that these interactions are happening at work is also factoring into the equation. It’s one thing to ask a woman out at a bar, it’s quite another to ask a woman out at work—even someone you work with occasionally. It’s all about implications and consequences. It’s one thing to get rejected at a bar, it’s quite another to have a work relationship blow up in your face. So as we answer your question, this variable has to be considered.

Ann, it’s time to be a detective. It might help your decision if you knew more about this guy. Is there anyone you can ask? Can you google him? The other way to glean information is hint around without actually saying it. For example: After he asks you what your plans are for the weekend, you could say something like, “So what are you doing this weekend? Are you taking your girlfriend out on the town?” You can get away with this if you say it in a flirty, joking kind of way. (We know you say you aren’t great at flirting, but we’re confident you can do this.) Based on his answer you will probably learn a lot. You might say to yourself, “Well, won’t it be obvious that I’m sniffing around?” And our answer is: Yes. But that’s not a bad thing. He’ll get a better sense of where you stand. So instead of writing him a note telling him how you feel, start by doing it in a circuitous, flirty way. If you learn he has a wife or serious girlfriend, then you’ll know his visits are strictly friendly. And if they’re not, then you’ll learn something about his character because that means he’s being deceitful, and trying to cheat on his partner.

The other tricky part of this is the fact that he lives in another state. He might be very interested in you, but not be interested in a long distance relationship. But if he got to know you better, he might change his mind on that. So question for you: What time of day does he come in? Would it be possible to take your break around the time he visits? Or go to lunch? We see no reason why you couldn’t ask him if he’d like to grab a coffee, or go to lunch. Yes, it might be a little forward, but it would break the ice a bit. And once you were away from your work environment, both of you might open up a bit.

If none of our suggestions work, and you’re still feeling like you want to reach out to him, then yes, a short note revealing your feelings would be okay. And if he doesn’t reciprocate, well, then the fact that you don’t see him that often will actually play in your favor because he won’t be around every day to remind you of the rejection.

So start by trying to investigate a little and see what happens. Be patient. Give this another month or so, and if things don’t progress with Plan A, go to Plan B. But remember, once things get rolling, he needs to be the one to take the initiative. It’s okay to break the ice, but after that, he’s got to be the one making the moves. (Asking you out on a proper date, etc.) Otherwise you’ll still be wondering where he really stands.

We hope this helps. Ask as many follow up questions as you’d like. Now, or a month or two from now. Leave us a comment/question in the comments section below.

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Good luck,


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72 Comments on Nice, flirty, interested; how do you tell?

  1. Thanks for the respose Guys

  2. @Liz….You’re welcome.

  3. So I met this guy last week at a party and we ended up talking all night and we left the party together. We hung out for the rest of the night and I ended up staying in his room until I had to go to class the next morning. I asked if he wanted my number, he said yes, and then gave me his number as well and I left. He hasn’t texted me since but he does acknowledge me if we pass by each other. I can’t tell whether he just isn’t really into me or whether he is just kinda shy and doesn’t know how to approach me. I just need a little advice from a guys prospective on whether I should wait it out kinda or just move on. Thank you for your time!

  4. @Kristen…..What actually happened in his room? Talk? Kissing? More? In general, you should let him initiate.

  5. Hi Guys!

    in October, I met this lovely boy in my biology lab. I had noticed him in lectures, and I’d found him really attractive, but never managed to say anything until about a week into the course. Anyway, I was able to set up lunch dates (that were never called dates) with him quite quickly, and we still meet up regularly. He is so shy BUT I LIKE HIM SO MUCH.

    So, he is confusing me. He is always so nice to me, and I think he cares about me. One day, we drove around for an hour and he was so shy and so awkward; another time, when he found out that someone at university hit me he was going to beat him up. He never texts first, but when I do, he does whatever he can to keep the conversation going. I noticed, too, once when he flaked for lunch (his phone switched off and he wasn’t able to tell me he couldn’t make it), he saw me talking to my friend, and he looked over at me when he thought I wasn’t looking, so I don’t know if that means anything. He is so very shy, and I wonder if that may be why he hasn’t been more direct. I also wonder if maybe I read too much into his behaviour.

    We were meant to hang out over a break, and I hadn’t heard from him all of exam week. So I messaged, and he replied and even asked how I was doing with regards to some BS that’s happening, which was nice, because it implies he pays attention, as I told him about it weeks before. And then he said we could go snowboarding, and if I didn’t know how we could “start new” on the flats. His alternate plan was for “all of us” to go get sushi. I told him it would just be the two of us, and he said that that was fine and that he isn’t afraid of me, and that he was just trying to be considerate.

    He has told me that he is a virgin and that he’s been in one relationship before starting university, but he doesn’t talk about it much. I don’t think it was anything serious, and I don’t know who ended it and why. I was the one who casually asked.

    After my boyfriend and I broke up earlier in the year, we talked about it. He said that he wasn’t sure why he would do something like that, and said that he hoped I was okay, and then he came to university the next day and he just sat with me. He asked how I was and I told him how I was starting to feel more and more hopeless with regards to relationships, and told him how it was affecting my self-worth and I told him I felt ugly and whatnot, and he told me not to think like that, and he really didn’t know what else to say. He was shuffling awkwardly in his seat. And then when we said goodbye, I hugged him, and he waited outside of class til he was sure I had a ride home. I know I really shouldn’t have said that, but I was very upset at the time, and I didn’t see him as a potential lover.

    He has moments like that where I question myself. One time when I was upset, earlier into our friendship, he told me I would always have “him, my friends at university, and my other friends”, which was interesting since he separated himself from the uni group. Oh, and when I got him his Christmas present (it was a shirt), he put it on immediately. And then he said he wanted to get me one, but wasn’t sure what I’d like. That was nice, because it implied he thought of me during the break. But I just can’t tell if he’s being nice or if there is more, there.

    I think the biggest incident that happened was when he and I went to a mall after class.
    He called his mom and asked if his younger brother needed to go to work, and he told her that “he was hanging out with a couple of friends.” When I called him out on that, he just said that it was easier to say that than to explain. We got on the bus and he was going to let me sit down while he stood, but the person in the seat next to the empty one was weird, so I stood next to him. And then he let me link arms with him when we crossed the streets and stuff. And I noticed that when I tried to poke his tummy, he actually touched my hand to stop me, he didn’t swat me away like I expected. This happened often, he even held my hand at one point to spell “No” on the table as a joke.

    I had to ask him to buy me lunch, because I only had a 50 to break, and he did. There was a man who made me very uncomfortable, and he asked if I wanted him to beat him up but I said no. Anyway, we ate and then I asked him to use my money to buy me a soda, and he did. He got up and bought it for me, and then he came back. He opened my sushi box and my pop for me because my wrist was sore. I bought him a cinnamon bun, and then we left.

    On the bus ride home we were talking and laughing at stuff, and he shared his cinnamon bun with me. And he still let me link arms with him even though he laughed at me for being such a loser. Oh, and when I handed back the cinnabon box, our hands kind of touched each other’s for a while and that was nice. We just sat there and he said I could have more of it, but I said I bought it for him, and the whole time our hands were touching. It was almost like he was helping me carry the box, that’s the best way to describe it.

    When we got back to university, I told him to walk me to the building so that “no rapists would get me”, and he said that he might be one trying to lull me into a false sense of security, and I said the sex was welcomed. He didn’t freak out. I walked with him a bit, and he said I didn’t have to take him to the parking lot. I asked if he was sure and he said yes, and we hugged goodbye.

    Does he like me? How do I approach this. I think what is preventing me from acting is his never texting first, and the lack of direct hints. I honestly can’t tell if we’re just good friends, or if he likes me. I don’t know how I could possibly make it more obvious that I like him, and I just don’t know what to do next. Thanks for reading all of that, there’s more, but I figure that I typed enough 😛 You guys are amazing, thank you for all your help!

  6. @Dee…….Thanks for your donation. First we need to understand the dynamic better. A few questions for you: Would you say you’re “out of his league” if you met at a bar or something? Meaning, would he say you’re too hot for him? Also, did you have a boyfriend when you first met this guy? And what’s up with all of this talk of weird stuff happening and him offering to beat people up? That seems odd to us. What’s going on with that? Finally, you say he’s shy, but is he also not very confident? Our initial impression is that he does like you but he’s unsure of himself. And he’s not quite sure where you stand even though you’re making it painfully obvious. (At least to us) Sometimes, when “relationships” begin a certain way—in this case as friends—it’s hard for them to transform into something else. Answer our questions if you could and we’ll get back to you later today and see if we can figure this out for you.

  7. Thank you so much for your response. I’ll answer those questions for you, now.

    1. I wouldn’t think I’m not out of league whatsoever.
    2. I had a boyfriend for about three weeks in January, but he didn’t know til after we broke up. When we met, I was single.
    3. I live in a city where strange things happen on a regular basis. It’s not really a good idea for a girl to walk around by herself, and he is very protective of me sometimes. He knows weirdos approach me often, and so he worries, I guess.
    4. I would say he’s not very confident and is painfully shy.

  8. @Dee……….Thanks for answering our questions. He sure sounds into you, but shy and not very confident. (Unless he’s just not into you at all, but we don’t get that sense.) This might be one of those situations that you’re going to have to take the initiative. Cook him dinner. Possibly hanging out watching a movie. Maybe make the first move with a kiss? Obviously you need to feel comfortable with however you proceed. It’s likely he feels intimidated by you since he’s a virgin and you’re not. If this is going to move forward you might have to be the one to do it. Keep us posted. And let us know if you have other questions.

  9. Can I ask what makes you think he’s into me, though? I would really like to know what indicators there are in his behaviour, so I know what to look for. I’ve always thought that there were mixed signals being thrown around, but always had a nagging suspicion that feelings were mutual – so, what makes you call this a crush, and not friendship?

  10. @Dee…..Indicators: Nervousness, touching, laughing too loud, offering to beat someone up, paying for dinner or movie, getting jealous of other guys. Of course, we don’t know him like you do. We can’t read his mind. Sorry, we wish we could. We still think you’re going to have to move this forward, or at least try. If it backfires, well, you won’t be any worse off than now. And knowing is better than not knowing. Take care.

  11. I’ve known this guy for a couple of years. He’s in his 40s. When we met initially he would ignore me, as time went on he would ask me silly questions and be flirtatious. Sometimes I would catch him staring at me. So, I figured he liked me. However, at the time he was living with his girlfriend. He broke up with her a year ago. We communicate by email periodically. He works in the theater. So, I’ve been to a show or two that he’s worked on. When I’ve seen him, we’re always cordial and friendly. I’ve been flirtatious with him but he just stares at me. I’ve tried to reach out to him by email to give him cues of my interest but he hasn’t asked me out. I was thinking about asking him by email if he’d like to go to the movies. I have free tickets and I always ask my friends to go. I’ve never asked a guy out and I don’t know what to do. What if he turns me down?

  12. @Dee….You’ll never know unless you try. However, if he hasn’t initiated something by now we’re wondering if he’s interested in more then friendship.

  13. Hey guys, remember me? I have a jerk of an ex boyfriend that I discussed with you a few months ago. Anyway, I’ve finally moved on and I’m trying to get myself out there. I moved across the country for the summer a few weeks ago and got a really great job at Spacex! I work as a barista and I also serve food at lunch and dinner. I’m very busy all day, usually I work 10 hour shifts. Before I started work, I went in for lunch with my dad (who’s the exec chef)and I met this great looking guy named Adam. He was standing there talking to my dad’s friend about hockey, and dad went to talk to him. Then he introduced me. When he first saw me he literally said “woah” and seemed floored and just looked at dad and was like “congratulations, chef.” then shook my hand and introduced himself. I don’t think he knows I noticed his reaction. And even I don’t know, now that it’s been a week, I’m worried I’m overthinking it and maybe he didn’t react quite how I remember it? I’m so worried that he wasn’t REALLY interested and I’m just flattering myself . . . anyway, the big thing is, he doesnt work in food. I THINK he’s head of construction or something like that. I think he’s really cute and funny and he’s got this awesome smile and he’s so happy all the time. But the only time I see him is when he comes to the barista stand to get coffee, and during lunch/dinner. All these times I’m working, and it’s super fast paced. I can only stop to chat for a few minutes at a time, so I haven’t really gotten to know him yet. But I really want to. I don’t know how to start talking to him more, and I REALLY want to go out with him. Can you please help?? Should I make the first move, or wait longer for him to ask me?
    PS – another problem is that there’s an age difference . . . at max, he’s 10 years older than me. I’m not entirely sure how old he is, but somewhere around there. It doesn’t matter to me, but it might to him.

  14. Small update: I haven’t been working the barista bar this week, so I haven’t seen him much and I’m worried forward motion on my part wouldn’t be very welcome now that we can’t talk as much. What do you think?

  15. @Grace…….First of all, how old are you again? If you’re in your early 20s and he’s in his early 30s he might feel pretty awkward about moving forward. If you’re younger that’s an even bigger dilemma. Also, remember, he knows your father. That’s a huge barrier here. He definitely doesn’t want to do anything to piss off your dad. And even if your dad was okay with it, he might still feel funny about it. We think this is just one of those crushes that you’re going to just have to enjoy privately. In general we think you should wait for him to make any sort of first move.

  16. Hi Guys
    This is a follow up question from Feb 2013. I recently saw the guy I was talking about and he told me he has been busy at work but is now free to come to the gym more often. He also told me I look nice and that I always look nice…. Was he just being nice or? I have not seen him close to 6 months and he said I always look nice?

  17. @Liz……Has anything happened this past six months? If not, maybe it’s time you to close the book on this and shift your focus.

  18. Thanks Guys

  19. Hi Guys! My parents and I had been going to this restaurant inside of a hotel we’d been staying in for a week. There’s this waiter there who I suppose is near my age and I cant tell if he liked me or was just being friendly. One day, when we passed by him, he had this big smile on his face and said “Have a nice day” looking only at me. Then once, when I was passing by, he seemed to be doing something on the computer, but was actually watching me-And when I looked at him he quickly looked away. Then, up until our very last day at the hotel, he’d speak to my parents and then to me separately. Is he just being polite, because he was talking to his coworkers today and this time when i passed by, he didn’t look at me 😕 Thanks in advance!

  20. @Lexie…….The question really is: If he’s into you what exactly is going to happen? Is there a chance you could even see him again? To answer your question: Yes, it sounds like he might have thought you were cute, but he works there. It’s very unlikely he’s going to do anything about it. Just enjoy the attention, but we don’t see anything coming of this.

  21. hi guys!
    i need help, so there’s this guy he never said he liked me. all what he did was text everyday and call and tell me what a special person i was. he cared alooot about me and then when my friends started annoying me about him being my bf i told him. he got upset and we just stopped texting over the break. when we met after couple months he was nervous but every time i meet him its like meeting a new person. i mean he keeps on changing his behaviour [he either ignores/ nervous/ talkative/ tries to make me jealous]
    i did not start any of this he chased me cause i do not throw myself at any man.he apologized afterwards but he keeps on changing his behavior. i do not know does he consider me a sis or a friend or what. plus whats up with the weird switch of act.

  22. Hi guys! I met this foreign guy and we were messaging via internet (about hobbies and such), but the messages sent slowly so he asked if I had Skype. I didn’t and had trouble making an account, so he offered to make 1 for me. I told him he didn’t have to go through the trouble but he insisted (and told me how to change the password). Then he offered any additional regarding the internet.. On the subject of hobbies, I told him I do theater. He said he doesn’t go often but would “for sure” like to see me in it. Next he spoke of how much it snows in his country and how some people rode sleds/sleighs. I told him it never snows enough to do that where I live and that I’ve got to do that one day. Then he tells me that if I were close to him, he’d “help me fulfill that small dream” and that he would pull me (w/ smiley face). He tells me I should come there. We talked for 4 hours and while it was only 10 pm where I live, it was 5 am where he lives. So he told me to take care of myself, “good night and sweet dreams.” Is he just being polite? Thanks guys!

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