I think spending $200 on two watches might fit the bill better for you.
I have a cheaper Timex Ironman that I use in the field/camping/hiking/swimming. It's been banged off rocks, submerged for a while in salt and freshwater, dunked in oil, and abused but it's always been working fine. Plus, the alarm and glow feature are great for camping or to wake up early to hit the trail/field work/job. It's cheap enough that I can junk it should it break- plus being digital, it's light. Yes it takes a battery, but out of habbit, I put a new one in once a year or so... $10 once a year is very cheap insurance to me.
Have another $150 classy looking watch for your dates and interviews. Keep that one nice and clean. Personally, I'm a huge fan of the Swiss Army watches. That will be my next purchase when I need a new "nice" watch. It will be fine if cought in the rain, but it won't see time underwater or in the mud. Some may blow your budget but some should be fine.
How often will you really be going from an interview or date straight into a mountaineering expidition.
Also, being that I know you personally, you aren't the easiest/kindest on any equipment. You tend to find flaws/weaknesses in things really fast and break them. Get something disposable or rugged for your adventures.