Is It Okay To Ask My New Girlfriend To Chip In?

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Q: My new girlfriend never offers to pay and I’m going broke. 
Will it ruin the romance if I ask her to chip in?

Big or small, whether dating or married, money issues can cause serious romantic ruin. Most of the resentment is around non-disclosure and could be avoided if both people know the score. In this case, she doesn’t know your situation, so could either be obliviously ordering dessert, or wanting to chip in but not hurt your pride. Hints don’t work. Tell her things are a little tight and propose eating in more, with the added bonus of allowing you both to expand your cooking repertoire. Get a little creative on dates (like a picnic, or a sunset hike) and suggest dates where there’s an opportunity for her to chip in – at the movies, get the tickets while she gets the snacks.