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.