As someone from Boston currently in Stamford who loves both, I'd lean towards Boston area for you.

When it comes to dating, career opportunities, even just going out to bars, you are going to get more and a greater variety of opportunities in Boston. You will probably get better projects in the Boston office, and if things don't work out with Deloitte you'll have a greater selection of other opportunities that don't require you to move.

Also, if you are a consultant, flying out of Logan is waaaay easier than fighting your way over to JFK or Laguardia. I'm sure your compensation will be enough to get by. Make sure you get the full match on any company retirement benefits (i.e. 401k) but don't stress too much about saving tons right away.

Look in Cambridge, Somerville, Allston, Brighton, Southie for housing. Anywhere on the red line or green line.

I played flag football for many years with BSSC and they do tons of other sports as well, very well run intramural sports org.

Don't get me wrong. Stamford is awesome, I absolutely love it. But I think it is a better spot for young couples and NYC commuters. Another option for you could be to live in NYC and reverse commute to Stamford.

To me, Stamford is like a moon that orbits New York. Boston is its own planet. In your situation, you want to be on a planet, not a moon.