96 Comments
 

I already responded to this post, but it disappeared. 

Don't show up at her dentist office. That is her place of work - she will be in work mode. Ask her out on a proper date.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 
wsomembersince09

But then how do I ask her out? I can't send a random message on LinkedIn as we are yet to be acquainted. That would look even weirder. This way I thought I could try to charm her on my first visit - to the extent possible - and if I see encouraging signs i can ask her out officially 

Oh ok yeah wait until you match with her. Don't stalk her. If you don't match with her, just let it go. On to the next one.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

this is pretty creepy. just stick to your career and find a sugar baby. ib/pe has no bearing upon your game, clearly lack of it 

 

No ib / PE has no bearing on your game. Did I say that? Those are your words. What it does do is a signalling effects - unless you're a dick, hopefully tells the other person you're smart, driven, and personable. Also, the more educated and driven a woman is, I think, she'd be more inclined to pick a guy whose equally well read and ambitious. Obviously cetris paribus. 

The only time in/PE has helped me is when I am at a cheap bar and some eastern European chick with poor English asks me what I do (given I dress up reasonably well) and then when I tell her she seems impressed even tho she prob didn't understand any of what I said 

 

Just wait a bit to see if she swipes right on you. About a week or so. If yes then you don't have to worry about this.

If no, then go ahead and schedule the appointment. Be natural and pretend like you never even saw her on Bumble. Then go for the ask. Life's too short to worry about little rules and formalities. Some times you have to be a little bold and enjoy the thrill of doing what most people wouldn't ever do. If it doesn't work out, then fuck it, you'll never see her again anyways.

 

good point - if you have more than ten cavities for example, its a signal that you aren't proactive, diligent, or conscious about health in general.  

 

May be less creepy if you wait for her outside of dentist office to go to lunch, follow her to lunch, and then “randomly” bump into her there.

Totally kidding. Do not show up at her work dude.

 

Clever analogy, but actually no on either. I’ve actually posted on the past using dating as an analogy for acquisition sourcing and deal closing. Advice to you: don’t obsess over the dentist. Take the experience for what it is: a realization you want to find more serious people. What you’re describing is a recipe for disaster. You need to put yourself in a position where you don’t feel the need to do something elaborate like courier a letter—that will not go over well. You want to find serious, single, accomplished women? Get involved in philanthropic/art/museum orgs, donate, go to galas, etc. Once you realize there’s plenty of people to meet, you can hopefully just be casually confident.

 
Most Helpful

Firstly, I was originally on here in ‘07 during the recession versus your ‘09, so hardly young. Secondly, I have extensive LTR and STR experience, and guarantee that you are probably imagining this playing out in some sort of “rom com” way—I am here to tell you it absolutely will not. If you do the first part of the plan, you need to be respectfully flirty, then ask her to grab coffee/drinks later to her face at the end. Delete your bumble account first. If you are what you say you are, and she’s single, I would take odds she’s going to be like fuck it and say “yes.” If she doesn’t, you will at least have nice clean teeth and the confidence boost from doing it to ask out someone else. Having a courier deliver a message looks weak, not “gentlemanly,” it’s like the adult equivalent of having your friend go ask a girl if they like you during middle school recess. You’re former banking/PE? You’ve had more at stake in high pressure situations, this is nothing.

 

Truly sincere question, zero snark intended, why is everyone in PE so vanilla or "by the book" on every topic.  Been noticing for years, finally decided to ask.  Sorry the roulette wheel landed on you.

I say this as a guy who works in PE myself (my job is 70/30 public/PE).  All my PE friends & acquaintances are always offering the most prudent take on every situation. 

I'm talking about prudence to an extreme level of consistency though.  A few examples just to clarify what I mean.  In any political discussion, PE guy puts stability and status quo above all else.  In any business discussion the PE guy is the most skeptical over someone taking a new or bold approach.  In any sports strategy debate (do you go for in on 4th down etc) the PE guy invariably favors the conservative strategy.  

I suppose someone could look at the nature of PE investments and draw the simple connection between stable businesses and risk-aversion outside of work.  But I don't really think of it as a career that attracts a certain personality type.  Not like how motorcycle racing or accounting would naturally attract a given personality.  PE is just basically the more successful end of the broader white collar sector that employs half of America.

 

I don't think your idea is creepy.  Many people will call it unprofessional or desperate, but those people are just uptight sheep who've never done anything unusual in their life.  Really there's nothing wrong with sending a letter.  I'd rather ask her out in person but seems that chance won't present itself.  Also, small thing, maybe just mail instead of courier?  Like what's the courier all about?  Her office mail will get to her.

What's more concerning is your comment that you're basically changing your approach because you're 32.  I'd say be careful what you wish for.  You're younger than you think.  Soon enough, you're going to find out how normal it is for a guy in his late 30's or even 40's to date women much younger.  Dating women your age is the riskier play.  There are always exceptions to the following, but physically & mentally, men age more slowly.  Typical 40 y/o guy I know today is the same guy I knew when was 30.  Maybe a few extra pounds and a bit less hair, at worst.  And usually more wealthy and successful.  No so for the ladies.  So just be cautious.

 

Imagine being as accomplished as you are and asking people on an online message board how to approach a fucking dentist.

Smh dude. Hope this is a joke post. 

Array
 

Creepy based on what WE know, but the dentist has no idea (and remember, it's only creepy if you're ugly). Forget the whole courier thing...what even is that?!. 

You need dental services anyway so just go for it. My only concern is that you've over rehearsed things in you're head, and have jinxed the whole plan already. 

Make sure your Bumble account is deactivated until after the appointment. At the appointment, be subtly flirty, drop hints and try to get her to reveal details casually, like this--

Dentist: What brings you in today?

You: Been a while since I've been to the dentist, (you guys are scary), and if I'm gonna get back in the dating scene, need a nice set of teeth. 

If you pull off the above smoothly, you'll seem down to earth, funny and charming, and she'll know you're single. 

After that, it boils down to luck. Hopefully as the appointment progresses, she makes small talk and asks about your job, education, HOW you're getting back into the dating scene, etc. Make sure you don't come off as pretentious when responding. If she brings up getting back into the dating scene, that would be the PERFECT opportunity to mirror (i.e. how did you meet your boyfriend)? What's that, you're single? Sounds like my lucky day! On the flip side, if she says she's taken (either old Bumble account or turning you down in advance) what else is left to say?

On your way out, give her your business card if you have one or figure out a plausible substitute in advance. Say "thanks for the cleaning, you know, if you grab coffee with me, that would make me a repeat customer." Reactivate your Bumble account a day or two later. 

If during the appointment, she's not receptive (e.g. hyper focused on cleaning your teeth, not making conversation) then she's probably not interested. When women are attracted, even slightly, they can't sit still. Don't try to force it and just cut your losses at that point. Luckily, people finding romance at "work" is common and not limited only to co-workers. 

If you decide to proceed, all I ask is that you provide an update (good or bad).

Any questions?

SOURCE: banging my therapist

EDIT: Don't hygienists typically do the cleaning? Hopefully you need a root canal or something. 

 

Okay but realistically though: 

  • Dentist: What brings you in today?
  • OP: Been a while since I've been to the dentist, (you guys are scary), and if I'm gonna get back in the dating scene, need a nice set of teeth. 
  • Dentist: Um okay but I meant have you noticed any pain in your teeth lately? Are you brushing consistently? Okay.. hm... hmm... I see. Now sir, open your mouth and keep it wide-open please.
  • OP: Aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaah
 

The dentist only comes to see you after the dental hygienist sees your teeth.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

I'd vote for waiting till your third appointment with her before asking her out. And by asking her out, I mean literally - asking her out in person by uttering those exact words, just so... No couriers, no dating apps, just converse with another human being. You're both in your early 30s, why turn dating into a game of hopscotch? 

Use those three appointments to get her chatting whenever possible, yet don't ever - under any circumstances - reveal that you came to her dentist office just to ask her out. Though some find it cute, assume that she won't for the time being. Instead, focus on getting to know her and get her to know you. Fish for a topic she'd like to pitch in for and slowly tilt the conversation towards a date. So, ask for her interests in movies, music, theater, favorite drinks - anything for which you can get "a couple of free tickets for." 

Since she is a dentist, she most likely wont' be a simpleton, so expect her to sense your attempts early on. If she still plays to your tunes, then you got a shot. However, nuance is the name of that dance...

 

It's alarming that everyone doesn't find this inappropriate. It's one thing if you randomly went to the dentist and took a shot and asked her to coffee, but you looked her up to find her place of work after she didn't respond to your Bumble 'like'. You can try justifying it however you want and look to WSO for validation, but this is stalker behavior. Don't do this- move on. 

 

I guess I should update this thread. lol

I went earlier today. She's an orthodontist. I thought it was going to be 45 minutes, but I spent only 5 min with her. The remainder was taken up by these xrays and waiting and talking to her assistant. It was a free consultation. Anyways, more importantly, it was professional and friendly (but not flirty whatev). She didn't ask me anything about my work, education, and so forth, but just discussed my teeth and the plan. She was also wearing a ring, but that looked a bit too ugly to be an engagement ring lmao I thought maybe I should sign up and make the move after the third session with her. So I called up my insurance provider and buzz kill my personal ortho are not covered by my employer. Buzz killlllllllllllllll......I am not paying 5K out of pocket and thus I have no reason to keep in touch / plan a next visit, so I am crossing this off the list.   

TLDR: dropping it.

If you do end up seeing this, please respond as to whether your employer covers your personal ortho. I was kind of pissed to hear that mine didn't and now I am wondering if they're being stingy. 

 

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"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

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