Original thread: https://www.reddit.com/r/relationships/comments/3rj49k/i_f29_own_my_own_business_and_do_very_well_for/

I originally posted this in /r/relationships and it was suggested I try RPW for help as well. I introduced myself on the appropriate thread here and was encouraged to share this link and my follow up post. I've made some progress, but would still enjoy some additional insight.

Here's what's been going on since my first post:

A lot of posters advocated online dating, but I took it a step further on the advice of a friend and chatted with a "matchmaker." Matchmaker is in quotes because the couple who run the business are less about hunting you down the perfect partner and more about getting to the bottom of what you want, what your dating style is, and making sure you're giving yourself the best shot to get what you're after. They also put professionals who are too busy etc. to really date with partners for an evening - like a date for a wedding or company Christmas party, what have you.

So I met with these folks last week, we chatted, then off I went on four "dates" over the weekend. I had a good time, listened to a lot of the reddit advice and played it low key when talking about my work. When asked what I do I said "I'm a Business Intelligence consultant" and left it at that. If they pursued the conversation I'd say that work isn't as big a part of my life as it used to be, now I spend my time (fill in activity here).

So on Wednesday I talked to the matchmaker/counselor/guru of all dating advice on the phone and she recapped the feedback from the guys I had gone out with. This is obviously not the whole of our conversation, but what stuck out to me and frankly surprised me was the regularity of this:

"Very sweet, very smart girl, but maybe a little too smart for her own good?? Anytime I asked her about work she'd defer to another topic, like I couldn't follow what she does. A little insulting."

"I googled her before our lunch. I already knew what she does, but when I asked her about work she said she was a consultant and moved on. What's there to hide? That was a little weird."

"Dropped her at the Park and Ride and she leaves in a 100K car (this part is not true, btw). I google her. I didn't feel great that she told me she was a consultant, like she had to spare my feelings after we talked about my work. Felt off."

I seriously paraphrased here, but the overwhelming theme was I came off as either deceitful or offensive by NOT talking about what I do. Who the Hell knew??

So later Wednesday night I went as the plus one to a company holiday party. The other "rent a date" and I met our guys for drinks first, then off to the party downtown. When he asked what I did I took completely the opposite approach as before and said "I founded my own BI company five years ago. Interesting to some, mind numbing to others, so you tell me how much or how little you want to hear about that. We did discuss it, we had a great time, he asked for my number and we're going to have lunch on Sunday.

We'll see. I'd love for some tips and pointers to keep the positive momentum going.

tl;dr: Set myself up with a matchmaker of sorts - after a few get to know you dates, we reversed my strategy of downplaying my job and made it one of the first things I brought up. The subsequent date seemed much more comfortable for everyone involved. How to keep the positive momentum going?