I wish we didn’t split the check

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Dear Meredith,

I'm a divorced woman in my early 40s. I've been dating for several years and recently met someone new around my age. Everything is going amazingly except for one issue that I'm debating how/when/if to bring up. Financially he is a little on the conservative side and feels more comfortable splitting everything. I've taken the initiative to pay for dinners and outings so he can feel more comfortable reciprocating in general. We see each other about once a week and have a great time with shared interests, conversation, activities, sex, and lots of affection. So far, the financial part is the only thorn I feel, but there are so many other glimmering positives that it feels like a tiny stone under 100 mattresses.

I don't want to ruin our precious time together by having this type of conversation, but I know we should discuss it eventually. We've been dating for four months, and no disagreements or conflicts yet. He has done a few really sweet things, like give me beautiful flowers and random gifts, but I really would prefer that awkward feeling to go away when the check comes at dinner. The most natural time to bring it up would be when the bill comes, but I'd much prefer to have the conversation in private. Please send any tips or words of encouragement to make this conversation easier! Also, having been married before, I get the idea that relationships are not perfect, so ... should I just follow his lead and accept the check splitting as a compromise? I miss that romantic feeling of being treated to a nice dinner without hesitation! But the other romantic and sexual elements are stronger than ever.

– Trying to find love again

My sister has a thing where she'd rather take turns paying checks than splitting them. She told me that long ago, and it's really nice to have dinner with her. Like ... we're never going to go to any one place that's a lot more expensive than the next. Everything winds up being about equal when we take turns. I like that system for dates too, assuming two people get past the first outing.

If you like it that way too, let this man know. You're not saying you don't want to pay; you'd simply prefer to treat each other. It can be more of a "this is what makes me happy" than "you're doing it wrong."

You also might want to have this conversation when you're not at dinner. Maybe the information would be better received after you've left a restaurant. Like, "Oh, here's why I paid."

Venmo has changed this process for a lot of people. I used to take a friend to lunch and feel nice about it, but now their portion often shows up in my Venmo, which I suppose makes life easier and more fair. Less fun, though. But that kind of app is another way around this, if he really likes to split a check. At the very least, you wouldn’t be putting two cards on the table.

But something tells me you won't have to resort to that kind of transaction if you're honest. I know you don’t want to rock this very excellent boat, but this is a simple statement about what you like. It's not so different than "I prefer windows in the car to air conditioning." It's a conversation, not a criticism.

– Meredith

Readers? How/when would you bring this up? How do you handle the bill?