Can You Date Your Roofer?

I don't know the rules of dating very well. I was in a relationship for over fourteen years and now here I am, single again and knee deep in this big new dating pond. There are some things I'm not too sure about.

Like, can you date a guy you're writing checks to?  The roofer?  It feels kinda funny!  Is he interested in me or the boost to his roofing business?

I've been doing the online dating thing for a few months now, going through phases where I give it a rest because it drives me a little nuts.  And then I come back to it.

I've been back on one site for a couple of weeks, and just happened to meet a guy who mentioned in his profile that he had a roofing business.  And I need a new roof.  And he was cute.

Long story short, he came to my house and gave me a bid and I picked his bid from the pool of bids that I got.  I wonder why?!

Since we initially met on a dating site it feels kind of odd to be writing him checks to work on my house.  If any hanky panky were to transpire before this business deal is done that would be REALLY odd.  To me anyway.  So I'm trying not to flirt too much! Let's get the business deal done first, then hanky panky ON!

He asked me to lunch and we went out for BBQ chicken pizza and brisket sandwiches while his guys were pounding nails into my roof.  He paid for lunch, and I paid for shingles.  It was a great lunch.

We've been texting off and on all day and after some flirting I said I hoped he'd still be around after the business is done.  And he replied, "YES" and then ABSOLUTELY!!!"  He went all caps and three exclamation points, so I think he means it.

Have you dated one of your contractors?  Not to jump the gun or anything, but I may very well marry this guy and it will make a great story, about how God damaged my roof with an act of nature just to introduce me to this guy.

I guess people meet in all sorts of interesting ways, and if ya feel it ya gotta go for it!  Right?  If you've dated someone who has worked for you in some way I'd love to hear about it.