I'm quite hesitant to tell this story and unfortunately, because I'm ashamed of myself, and for privacy reasons I had to create a new account for this but I wanted to tell the story of the day my mother fell in love with me.

Long story short, many years ago I was working for a provider that was building algorithms for various dating websites.

The goal was simple: Increase signups.

A Little Bit of Background
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As a small group of rather "creative" engineers in their early twenties encouraged by large sums of money we came up with the idea of building "Matching Personas" which would be able to have a basic conversation, as well as have similar interests in the target subject.

Keep in mind that some of those dating sites have various "upgrade" (read payment) paths. Some had a "3 private messages" limit so that you can start chatting with someone but to continue the conversation, you needed to upgrade to premium.

The typical path for a user was:
1. Visit the website and search for what they're interested in
2. See a few profiles and decide whether online dating was their thing
3. Invest personal time creating a profile and putting down their interests, photos, etc.

Point #3 is where the magic came in.

I had been working on automating the creation of accounts, and more importantly the creation of what we used to call smart-accounts. After a few months we had increased the conversion rate by about 30% on average (Which is MASSIVE) and our internal funding was getting larger and larger. Our smart accounts ended up being able to recognize certain items in photos, understand the interests of new users, have "similar" interests that are either the same or tangentially related, similar number of kids, etc. etc.

Based on real matches we built an engine that learnt what people look for when they convert. How the conversations go, the type of language used when discussing, the similarities in interests and family, etc. Honestly a really wide set of super interesting machine learning problems from object recognition to natural language processing to recommender systems to LTSM, etc.

It was pretty simple. A user signs up and they put some of their information in. Our engine picks up the latest user's information, creates about 10 different "smart profiles" that the new user is likely to match, and then in the search results display those smart-accounts to the new user who just joined. The new user would see smart accounts, and start chatting with them on their free accounts. Because we knew based on previous real matches and real conversations how people ended up "being together", the unsuspecting free users.

The conversion path was: Signup -> Fill profile -> See someone you like -> Converse -> Upgrade.

The Day my Mother Fell in Love with Me
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Now that you have a little bit of background, the story begins. I had been working for many of the dating companies (most of them competitors) for a few months and our smart-profiles were getting quite clever.

One night after my mother invited me for diner. We started eating and drinking wine and just talking in general. I never talked about the general aspects of my work but she knew I worked with computers and back then statistics now machine learning now everything-is-AI-anyways.

Whilst on the topic of computers, she said: "Oh I haven't told you, I've actually met someone online". I didn't think anything of it, I thought it was quite nice.

Then she proceeded to tell me the following: "He also has 3 kids, he likes a lot of the same stuff I like which is really nice, and we started chatting and he's really nice. He's gone on a business trip now so we haven't talked in a few days but I'm looking forward to talking to him again".

At that moment I became very suspicious because all the signs pointed to exactly what we had been aiming at achieving. Get users to like someone, signup, chat (Which had a limit of 50 free messages at the time for that particular platform if I remember), and convert (pay) to have more chats. The trick was when people upgraded, within hours, we had some canned answers like "I'm going on a business trip won't be able to talk for about 2 weeks".

Either way, I started asking my mother a few more questions and she explained to me that she had found him after signing up and they chatted a little bit but she had to upgrade yaddi yadda and it wasn't cheap but she was glad she didn't end up wasting so much time online dating like all those other people online dating. Then I asked her about the particular website and it was one we had been working with.

She had actually fallen in love with my bots. I felt terrible not only for my mother but for the thousands of other people we had basically scammed, and only at that moment did it hit me. Up until then it was a fun challenging ML engineering problem with real-world subjects.

I quit the following day and have never been affiliated or interested in either working or using online dating since. Even though I do have friends who got married to people they have met online dating, it made me a cynical.