If your relationship goes as far as a fifth date, you may be making emotional investments in the other person. Before you let your heart outpace your head, take a breather and find out about this person’s current and future financial picture. A few direct questions or a casual but targeted conversation can reveal most of what you need to know. Avoid allowing this discussion to become an interrogation.
Check out his or her career expectations.
It is not out of line to ask where your date works and what the job there involves. You probably picked up this much in the small talk from the first date or two. If you are moving into serious thoughts about a more permanent relationship, you need to discuss whether this is a permanent position or a career stepping stone. Try to get a clue about the current income level without sounding like you are probing too much to soon.
Does your date have a decent work history?
It is one thing to have a job and another thing to keep it. If you are regularly hearing stories about how each of the person’s 19 jobs have ended with an unfair move by the boss or being framed by coworkers, consider this a serious red flag. Ask yourself if you want to be hooked to a person who is always losing their source of income.
Talk about personal credit and debt.
Are the fabulous wardrobe and special gifts supported by salary or debt? Is the person making enough to support the current lifestyle or is it an illusion propped up by several near-the-limit credit cards? This might be a temporary situation due to unexpected expenses from another source. If it is a lifestyle choice, you may want to think a while before going forward in this relationship.
Try to get a view of total debt.
Mortgages, car loans, and student loans are still debt that must be repaid. If you decide to make the dating arrangement into a permanent gig, your date’s debt will become your debt, too. This will probably not be a deal-breaker in most cases, but you need to move forward with your eyes open.
Ask about the future.
Most people have at least some tentative goals established for their life. Look for markers like five years or ten years out. You are looking for career, financial, and personal goals that may affect your future security. Not all goals will be reached, but it is important to have a target to aim for.
Where do you see your spouse’s role in the family finances?
The answer to this question may vary by gender and tradition. This is a question that will have to be evaluated on your personal expectations and practicality. A women who fights for the rights of women may not want to be supported by a husband. A chivalrous man may want to be the sole provider. The main purpose of this line of discussion is to make sure that you can both agree on what is acceptable and practical.