Damn! Everyone's so guttered in finding that elusive soulmate. In the intended pursuit of marriage, the questioning of financial undertakings of the prospected spouse is not too gross nor is it misbehaving to probe each other of their combined wealth. That inquiry is the most organised and forthright in such conventional partnership. Hey, what are your constraints and prospects? However, the Homo Hybrid 2.0, having acquired the taste of woo-ship and the resolution of partner-ship is straddled between competing goals. Wanting to experience that falling for someone, yet, not willing to overlook the economic disparity in the lead up to marriage. At least in that guise of suitability matrix, that financial inquiry could be brought forward, once that is satisfactory, both might further their interest in each other. The challenge is greater in the modern times with dating and pursuing that liberal sense of organic attraction. Tricky on the first date, unlike the confrontation seen earlier, both have to infer the money matters through observation and etiquette. While the man is jittery in offering to fully pay the dinner without misjudged as patronising the woman, she, on the other hand, does not want to invoke the suffragist in her intimidating the man. A bit of snap and pull ensues, I will pay, that's alright, I will pay. I want to pay. I do. Who should pay the first bill, because it sets an impression in chivalry for the man and in esteem for the woman. A slight mishap in that 'snap and pull' could upset the budding interest. Splitting the bill is un-charming! And vacations?! Brooklyn and Tacos are manageable with less awkwardness but what about that Sharm El Sheikh for the Memorial Weekend. Bells and trance, still only a year into the developing relationship, not wanting to jeopardise, not willing to assert, it takes nurtured years to even out the generous or lop-sided planning. How do emerging couples split their holiday expenses. Honey, you do the ticketing. I will take care of the Airbnb. They are just warming up in the relationship not wishing to sour it by confronting the Black-Scholes-Merton formula in pricing the dating option. Are they in-the-money or out-of-the-money when they call the relationship quits. The modern romances juggled in financial planning of dinner and holidays is challenging over the book keeping in customary match-up. Not unmannerly to inquire the other's financial contribution to the household, but how is one to inquire: Babe/Cuddly Bear, have you paid in advance for the sightseeing? One can get away making gainful inquiry in the propositioning setups, but the starry-eyed modern daters are dumb-founded in credit swipes not risking the fate - she/he is the destined love of my life!