#677 Was that a date, or, “Should I forget about her and move on?”


I am a man in the late twenties, who have zero dating experience.

I have recently met an insurance agent on the street who approached me to get my contact. Even though I mentioned to her that I already have my insurance adequately covered and personal agent whom I trust a lot and thus is unlikely to be getting anything else insurance-related from her, she remained friendly and said that she would still like to meet up for coffee one day and thus I gave her my contact eventually.

I have to admit that I was rather apprehensive at first since I was familiar with the insurance agents’ ‘modus operandi’. They would generally position themselves along the busier walkways and utilise a ‘throw everything at the wall, some will eventually stick’ approach by striking up a conversation beginning with a survey to get a brief outlook of your financial status and then arranging a meetup so as to perform a personal review and then to persuade the other person to take up policies from them. This is so as they are generally paid based via commission and have a target to hit every month.

As such, knowing myself that I would not be taking up any policies for certain and so as not to waste the other person’s time, I would try to avoid them or just decline politely. As in this case I was already upfront with her, I thought that there’s no harm meeting up just on a friendly pretext if she wants to.

Subsequently, we met up twice over lunch. During the first meet-up, we chatted a bit and eventually, she turned the conversation towards my financial position and on giving a second opinion. Once again, I reiterated my position (especially in addition to the fact that I’m currently taking part-time studies and am really strapped on cash).

Still, the whole lunch appear to go over quite well and I was keen on meeting up with her again. I asked her out over text and she agreed. The second time, we just chatted about stuff in general and did not mention anything insurance related at all.

I thought that things were going well, however, my past two attempts at getting to meet her up again have been faced with her attempting to postponing by mentioning that she is really busy with work. In our last correspondence, she even mentioned that unless it is to meet up for ‘business’ even though she ended with a ‘just kidding’.

Should I just forget about her and move on? I should mention that I’m a very introverted person in general and rather bad at reading social cues. Thus I have a hunch that my optimism was misplaced and that she actually just viewed me as a potential customer.


Head says yes but heart says no.

Dear Head Says Yes:

You had a sales coffee, a sales lunch, and what sounds like a 95% sales meeting/5% date lunch that didn’t go anywhere. That 5% calculation is because on that second lunch she may have had some real “what the hell, he is really nice, let’s see what happens” inclination in treating it more as a friendly/date sort of event mixed in with a mercenary grab for your business. Maybe. I think there are people who don’t go on any dates with a person until they’ve really made up their minds that they want it to go somewhere and other people who say “Sure, why not?” and then figure out their feelings on the fly. The clear signal here is that when you tried to schedule more outings, she declined and redirected 100% you back to business (“just kidding” or not, that’s what she did).

Dates and “dates” that don’t go anywhere are very, very common. To me, first/early dates are for spending time with people who seem initially exciting to see how you really connect and to see if that feeling holds up when you’ve spent a little time together. Rejection never feels awesome, but as you accumulate more experience, the dates that don’t really pan out become valuable sources of information. Something about her caught your eye, or something about your personality was attractive to you – what was it? Would you recognize it again if you saw it on someone else? Now you know what it looks like when you don’t quite connect with someone: it’s really hard to schedule things, you can’t tell if it’s really a date, you sense ulterior motives, they don’t enthusiastically respond to your invitations. I award you 50 dating experience points.

This isn’t a rule, but it’s something that might help you keep perspective and budget your emotional investment (to the extent that we can ever do that) when you are trying to get to know someone new and you’re unsure whether they are on the same page:

If you try TWICE to schedule something with someone you don’t know very well,

AND they decline both times,

WITHOUT offering up an alternative or making a visible effort to make something happen,

…give yourself permission to stop making an effort to get onto their calendar.

Don’t do anything dramatic, or say “Guess you must not have REALLY wanted to go out sometime” or otherwise press the person for reasons or reactions. Just stop trying. You didn’t do anything wrong by issuing invitations, but either the other person isn’t interested enough to make you a priority, or they are interested but don’t have the bandwidth right now to make you a priority. Either way, the fact is that they aren’t making you a priority, so stop scanning “no” for signs and traces of a yes. Then, make a conscious decision to switch your focus elsewhere: on another new friend or date, on a hobby, on a great book you’re reading, on showing up in some way for the people you already know and love. Either the object of your attention will track you down when their schedule clears, or they’ll drift back into your orbit in some serendipitous way a few months down the road and you’ll have the opportunity to try again, or they won’t. If you can learn to be a bit easygoing about this, you will come across as a very relaxed, chill dude who is not afraid to ask someone out but who doesn’t hold on too tightly. That’s an attractive quality. It’s also a good way to practice self-care, by saving your time and attention for people who reciprocate.

There are no guarantees in life, but I think that someday somebody is gonna love you, and they are going to do it without trying to bag and tag you for their insurance client roster first. You’ll know it because your head and your heart will both say yes, and her answering yes will ring you like a bell.




33 thoughts on “#677 Was that a date, or, “Should I forget about her and move on?”

  1. LW, I’d just like to say that I am a little angry on your behalf. From your letter, it was clear to me that this woman was just using you, and I think 3 dates was a really long time for her to have done so. I understand that she works on commission, but it just seems like such a skeezy thing to do to go out to events that were CLEARLY dates (3 times!) just so she could get you as a client. I’m sorry that you encountered this.

    I’m also proud of you. Proud that you didn’t fall for her tactics, and proud that you never completely dismissed the voice inside you that was like “Heeeeeeeey buddy…we should keep our wits about us”. I’m proud of you for being brave enough to ask her out on a date after the coffee hang-out. I’m also proud of you for not ceaselessly hounding her to go on a fourth date; instead, you asked for guidance from a source you trust to get a bit of a reality-check. The behavior that you have demonstrated throughout this situation will serve you well in the future.

    The Captain is wise when she urges you to look at this as a good experience that will supply you with information for the future. Just know that from this random observer’s viewpoint, you handled this well!

    1. I don’t think the insurance agent did anything wrong–a lunch meeting with friendly chitchat isn’t necessarily a date. And I thought LW said they only met for lunch twice, and the first conversation was focused on finances. I understand the LW’s confusion, though.

      1. I’ve never done insurance sales, but it sounds like a sketchy way to do business to me.

    2. I don’t really agree that all three were CLEARLY dates — I think that the one in which business was not mentioned was clearly a date. The other two, I’d have to say were a non-meeting-of-minds: a date on the LW’s side and a business meetings on hers. But I don’t think she was doing anything unreasonable in treating them as business meetings; and I *certainly* don’t think that she was being deceptive or anything, and acting datelike at the time and then dropping the LW later.

      She made it very clear on both occasions that she was trying to have a business meeting… she brought up the insurance situation, and only let it go when LW told her to. It is not her fault if that is not what the LW was attempting to have.

      I totally agree with the Captain’s advice to back off and focus on other things, though. She’s pretty obviously focused on her business right now, at least with respect to LW. Either she’ll change her mind sometime and drift back into LW’s orbit or she won’t, and either way she’ll make the next move if she’s really interested (or later becomes so). If she doesn’t do so, it’s not because LW didn’t keep trying a tactic which obviously wasn’t working; it’s because she doesn’t want to in the first place.

    3. I think you are overly harsh in labeling this woman a user who tried to turn dating the LW into a business venture, especially since their first interaction was in a professional capasity and she was upfront about the fact that she was after his custom. It’s possible of course that she realised his atraction to her and tried to use it, but it’s also possible that she is too enthuciastic about a new job or too inexperienced to realise the boundaries of professional socialising, or that she has been given bad advice about how she should go about selling her product. Also, it’s possible that she too was looking at these outings as dates, but when she decided to break it off for whatever reason, she found it best (easier) to hide behind their professional relationship. In any case, thinking bad things about her isn’t going to help the LW in any way.

      1. Fortunately we don’t have to meet the standard of reasonable doubt here. Her true motives a) are unknowable and b) don’t matter in the end, only her decision and what the LW does now.

    4. I think you’re reading the number of meetings wrong. She got his number & info on the street (for business, clearly–sure he said she wasn’t interested but the whole point of a subsequent meeting in a gig like this is to change your mind) and they set up a lunch. There was no coffee. Coffee was floated as an idea–because when she’s pitching a customer “let me get you a coffee and we’ll talk” is way easier to get people to agree to–but they ended up going to lunch.

      Which was a business lunch.

      Then a second lunch, non-business, after which she stopped making plans with him.

      So, two meetings, not three.

  2. If you can learn to be a bit easygoing about this, you will come across as a very relaxed, chill dude who is not afraid to ask someone out but who doesn’t hold on too tightly. That’s an attractive quality. It’s also a good way to practice self-care, by saving your time and attention for people who reciprocate.

    This is super true! And it is also the exact opposite of the toxic lie of “romance”, which is that men “earn” women’s affection by being persistent and refusing to take no for an answer and by making grandiose gestures when women rebuff them.

    1. Yes x a million. I have sometimes wanted to go back and give someone a second chance after realizing I rejected them too hastily – but if they were creepy and didn’t handle rejection well they put the nail in the coffin. Good job, LW!

  3. Hey LW – it seems like the best course right now would be to assume this isn’t what you want it to be and let it slide. Perhaps she really is just busy and will come back to you later, but probably not, and hey you lose nothing by mentally moving on – you both still exist should curcumstances conspire to bring you together in the future.

    Anyway, this stuff is hard! It’s true of many things that everyone says no until eventually someone says yes. Like dating and job hunting and getting something published and so on and so forth. That period of hearing no is hard to sit through, no one likes being rejected. For me I’ve found the best approach is to give it your best shot, put yourself out there, and then instead of waiting and focusing on that one opportunity focus on the next thing while you wait for this thing. Clearly you like the idea of dating someone nice! You could try to pursue that more if it feels like something you could enjoy! Ask people out, date online, there’s a lot of great advice here on this site for how to go about it. Then if insurance lady comes back, yay! If not, you’ll be working on other options anyway, and can shrug and try with someone else.

    Also, ugh, I hate it when people try to socialise their way into a business deal. It’s always slightly misleading and disappointing when you realise that’s all they were doing. 😦

    1. I hate it when people try to socialise their way into a business deal. It’s always slightly misleading and disappointing when you realise that’s all they were doing.

      God, yes. I mean, if you’re smooth enough to make it obvious that that’s the goal but also be friendly and cool anyway–skills you need to be a king extrovert to pull off, that I’ve noticed–then good. But slipping the sting in after you made it look like you were just being nice? That’s some freaky cult-recruitment-level shit right there.

      1. In my fast food jobs, the bosses would urge us to use friendliness to get the customers to buy more stuff. I rarely did it, and whenever I did, I felt really gross. I basically tricked people into buying unhealthy food that they didn’t even want.

    2. “It’s true of many things that everyone says no until eventually someone says yes. Like dating and job hunting and getting something published and so on and so forth. That period of hearing no is hard to sit through, no one likes being rejected.”

      This is spot on. I am a high achiever who had some things fall into place easily when I was younger, but eventually I got into territory where the going was harder and rejection more common. This definitely applies to getting something published, which I have mostly avoided trying through fear of rejection. It’s important to remember that this is normal and not beat myself up or give up.

      It is of course important to remember that more is called for than mere dogged persistence and I am grateful to the Captain for the advice on reciprocity in dating and friendships. I have really appreciated learning about soft no’s and enthusiastic yeses. I knew those things instinctively on some level but it was so helpful to see it put into words. It helped me understand what was happening in a situation with someone I recently African Violeted, who was accusing me of being a poor communicator but in fact was not hearing my soft no’s. I thought I was an over-considerate wimp and now I know that soft no’s are natural communication! 🙂

      And I agree that socializing one’s way into a business deal is sketchy and flirting/taking advantage of the fact that the other person seems attracted to one is really dodgy.

  4. I’m sorry things didn’t work out they way you’d hoped for. You seem like a very nice person and I wish you all the best in future romantic endavours.

  5. I have to say I’m feeling pretty creeped out by the insurance agent here. If someone has said they’re not interested in your business, but agrees to meet up in a friendly and/or romantic context, and then you push your business on them anyway, that’s emotional exploitation.
    I’d counsel Running For The Hills, and deleting and blocking all forms of contact.

    1. I recently had an insurance agent show up at my door at around 7pm (I live alone) and use every trick in the book to try and worm his way into my apartment. First he wanted water, then he was curious about the layout of my apartment, then he asked me if he could smoke weed with me because he insisted he could smell it. When I told him I don’t smoke and the smell was probably coming from the floor below, he said he could go get some weed from those guys and we could smoke together. Eventually, I just had to shut the door in his face. I mean, I know working on commission is a tough gig and establishing a rapport is part of the job, but holy hell, I was so creeped out by the entire encounter.

      1. Jeez: any sales agent who comes to your door uninvited doesn’t merit any kind of hospitality. Ever. If they don’t like having doors shut in their faces, that’s all on them.

        1. Totally agree. There’s nothing wrong with a certain degree of politeness–like saying “No, thanks!” while shutting the door in their faces–but hospitality is not required.

          But I can’t get myself to find that this was creepiness. We don’t have the details for what was said in that initial conversation, but it doesn’t sound like she made it sound like it would definitely be a date. He even said that he knows the typical insurance agent’s M.O., so he generally avoids them so as not to waste their time, but in this case, he thought it was ok since he was upfront about it. So it sounds like he was already aware that this might be a selling tactic, and he was more concerned with wasting her time. So I don’t that I’d say that this is emotional exploitation, at least not any more than any other sales tactic.

          1. I agree. Overall, it makes me sad that we live in a world where a certain amount of emotional exploitation/boundary violating is a sales tactic (in many areas, it’s THE sales tactic), but I don’t think we can blame insurance lady for that, whatever her personal motives. Tattie’s comment just reminded me of that legitimately creepy insurance agent – he really did scare the crap out of me.

          2. @tinyorc Yeah, that dude sounded scary. I would have been freaked out for sure.

      2. Oh Jesus, ew.
        I know it’s a tough gig, but salespeople who use such people tactics are so skeevy because you’re actively wriggling your ways into the cracks of politeness and awkwardness and uncertainty that people (esp geeky or shy people) use to navigate social interactions. It’s exploitatuve and rude.
        I feel that this lady was doing that with you in part, but we can’t know. But I’ve experienced plenty of ‘hey…is this a date?’ Moments and it’s good to have experience under your belt. Good luck LW you sound like a nice guy 🙂

        1. Also, can we use “tries to sell me insurance when I … am out shopping / am in the library / am hanging out with a friend / have already said I’m not interested / thought we were on a date as friends” to explain things to “well, I wish someone would hit on ME!” guys? Because it’s the exact same thing!

          Also, how awesome would it be to learn some totally fake sales patter to use on guys who won’t leave you alone in public spaces, so if they won’t go away you start trying to sell them insurance? I am totally teaching my daughter to do that.

          (LW, I do not mean by this that you have done anything wrong! You are fine. You are not the guy I’m talking about.)

        2. Yes. Some of these selling strategies (and my own bad experience was with financial advice/life insurance sales) can be really misleading or triggering to people who have been stalked, or subjected to abuse at the hands of boundary violators. Like the “don’t take no for an answer” or the “push for a social connection and then leverage it into a business connection by making the person feel like they’re violating a rule of etiquette if they say no to your pitch.”

          A couple of years ago, I got a call out of the blue from a former work supervisor who wanted to have my husband and me over for dinner. We used to meet for lunch occasionally when we worked together, so it was just enough within the realm of plausibility that I said yes. And she still works in the business I’m in on the client side, so I didn’t want to burn a bridge. But then she launched into a 45 minute diatribe about my finances, complete with intrusive questions about what my balances were in my savings accounts, and how much I contributed to my retirement every year! Of course I didn’t answer her, I said I’d have to talk it all over with spouse. I sent her an email the next day saying we weren’t interested and were going to be too busy for the dinner.

          She continued to call me and email me every day for three weeks, leaving messages like, “I’ve bought all the ingredients for our dinner, when are you coming over?” like I’d never said no in the first place. Her messages sounded like Gordon Ramsay scolding an apprentice chef. It was awful. She even called me from other numbers, so I couldn’t avoid her using Caller ID. I ended up having to screen my calls for months.

          1. Trying to reply to cinderkeys here – You know, It really speaks to how little she must’ve respected me when I worked for her. She really thought I was that much of a doormat that she could eventually bully me into making her my financial advisor. LOL, nope.

        3. Yeah, agreed. They are relying on the fact that YOU will not break the social contract.

  6. One of the things my partner and I have running is a steady rule: we don’t buy or give door-to-door; we don’t buy or give over the phone; and we don’t buy or give to people who “ambush” us in the street. (Nothing against the companies and organisations, just not keen on those particular tactics). Making this clear at the start of the discussion can sometimes help discourage persistent sales types, and may prevent future such misapprehensions.

    Quite frankly, in a case like this, where the person you’re interested in mainly starts off interested in the contents of your bank account and the impact of getting you as a client on their bank account, I’d be saying “let them make the running”. Or in other words, let them prove they’re interested in you outside a work-related context. She isn’t interested in you except as another commission – and even in that case, she’s decided you’re more work than the commission warrants.

    Shrug, and move on.

    1. I agree with your steady rule. I don’t like to be approached on the street, so I won’t give money to people who approach me on the street.
      Sort of like how I give money to street musicians – but only if they’re in tune.

    2. I have the same general rule, although I do occasionally make exceptions for kids who I know are shoved out there for fund raising. But adults? Never.

    3. Where I live (Europe) the people on the street are almost always chuggers (charity muggers). I’m really surprised they find it worth their while. I sometimes say “no thank you” and keep walking but I also feel free to blank them because they are so annoying and their behaviour makes me NOT want to give to those charities.

    4. I make a point of telling sales reps, before any major financial decision, “I will need a couple of days to talk this over with my husband before we make a decision, so please can you give us the details in writing for us to consider.” Especially if it’s the sort of thing where you have to let them in your house to take measurements. The different reactions that stated boundary gets are very illuminating.

      For example, the heating salesperson whose immediate response was “don’t you control the purse strings then?” did indeed go on to push and push and offer me a “quote” which was a monthly repayment, not an actual total or a loan term or an interest rate (and when I did get a total out of them it turned out to be twice as much as the next nearest quote). If I had that experience over again, I like to think I’d throw them out at that point and say “you just lost the sale, go away now.”

      A window company we used were the absolute best: they came in and measured up and went away immediately. The quote came in the post a couple of days later.

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