My dad always used to tell us don’t be afraid to take chances. Life isn’t worthwhile if you don’t take calculated risks. Go for it.
And we all have heard the wisdom about one regrets the things they didn’t do.
I make a mental list of pros and cons and worst case scenario if I go ahead with something and that’s how I decide. Always knowing worthwhile opportunities involve some measure of risk. Don’t t live life being afraid. Life is short and if the pros outweigh the cons and you think it’s worth it go for it.
Where does he see himself in 5 years? 10 years? 20? What will help get him there?
Does moving in with the GF cause him to give up on a job that is his dream? If so, think hard. It may be worth it if he truly loves her but would be a shame to miss out on if this is passing.
Which job will help his resume get him where he pictures himself?
Look at pay, insurance, 401k matching, time off, on call requirements (if any), etc and see if one stands out above the others.
For the relationship, have they discussed the big topics? Do they both want (or not) marriage to the right person? Do they both want (or not) kids if able? Do they have compatible views on spending/saving? Compatible views on raising kids if they want? Similar pictures of the future? Do either have to move to make their dreams happen? If so, is the other okay with that? Do either have (or plan to have) expensive or time consuming hobbies? If so, are they compatible or will they the the drunk resentful person at the holiday party for that activity? (Saw this recently. Very sad!)
Job—I’d consider culture and people I’d work with including the manager to be one of my biggest priorities, followed by opportunities to learn and/or advance, pay, and prestige (prestige is really only important to me in that I’d want to have good exit options and working somewhere prestigious can help).
On moving in with the girlfriend—does he want to? That one seems more simple. Do they want a future together? Is the relationship working?
My lifestyle has been a bit different, up until 5 years ago.
I was a single mom, and every decision I made was made to benefit my children. If the decision was right for my kids, it was right for me. That is how I lived my entire adult life...until DH came along.
Now that I’m married & we have a blended family, with adult children in college, and in the work force, we tend to consider long-term effects of our decisions, and how any financial commitments we may make effect tuition, extra costs, etc.
When you have children, consistency is vital. Both of us sacrifice for our kids, so we tend to put their needs ahead of our own, sometimes, more than we “should”, but we share the mind set that everything we do, we do to encourage our children to have a better life than the one we have. We have a great life, but we want more for our kids. I believe the majority of good parents will agree, and relate to that mentality.
Moving in with someone is wise. If you’re considering a future with someone, best to get to know if you can live with them before taking the even bigger plunge of “happily ever after”. You can love someone like crazy, but living with them just may drive you to insanity. Better to find out now, than when it’s “too late”.
I also make a list of pros and cons. Let it set for a day then review my list, make any changes and go with the logical choice not an emotional one. I also believe to follow your gut; if it feels wrong it then it's probably not something you should do.
With the job choice I’d write down a list “for” and “against”.
He needs to know what things matter to him most ie most money, best health care, best chance for growth / promotion within company, closest to home and other benefits.
Then I’d rate each job as “1”, “2” or “3” for each of my important good criteria and reverse the points allocation for the negative aspects ie the worst score is a 3.
Then the job with the “lowest” score has the more to offer what’s important to “me” and I’d choose that one.
As for the girlfriend, a similar list of pros and cons for doing so plus taking into account if he is “ready” for a higher level commitment or not.
All that said, some people always go with their hearts !