Money, Love & Dating

One of the more awkward aspects of dating has been how to handle money. After two decades of marriage these are unfamiliar waters.

When I was young I assumed if I was invited out by a man that he planned on paying for it. If I invited him I would pay for it. For trips we would both pitch in. Typically, I would only invite a man out if I had tickets to a game or concert, or a special event. In these instances my date would contribute by paying for dinner or parking.

One time, I was set up by coworkers on a blind date. I met said gentleman in a Chinese restaurant (his choice) where he ordered a startling amount of food. Chinese is not my preference, so I ate little and watched him eat. When the bill came he asked me to split it and I quickly pulled out my credit card because I had learned enough to know I would not see him again. Still, I was flabbergasted when he had the food wrapped and took it all with him. I felt like I had bought him dinner twice.

After my first engagement ended I went on a great number of dates. I was living in San Francisco and ran into many people through my work, friends and hobbies. I went through a period when I accepted every date I was asked on. My friends called this my “serial dating” stage. I thought it was possible that I might find a diamond in the rough and I didn’t want to miss it. I dated sea captains, lawyers, tech guys, bankers, more tech guys, and an ER doctor. I was living in Russian Hill and the city was full of interesting people and I had time on my hands then, unlike now, where my days and evenings are full of work and family.

These were all mostly first dates. It was fascinating to be sitting across from a soul listening to their stories and learning about their interests, hopes and dreams.

San Francisco can give you the feeling of being surrounded by people, but also being completely alone. I spent that year alone looking out over San Francisco Bay from my Chestnut Street apartment. My work, the beautiful city and dating so many people provided the backdrop for one of the most formative periods of my life. By the next summer I was engaged.

When my late husband and I were dating he paid for most of our dates, but he made twice my annual salary. He even paid $1,200 for my car to be repaired and told me not to worry about it. Later, when our finances were combined and I made as much or more than he did he said it had been a very good investment. Men do invest in what they love and in the early years this was especially true.

Now, as an independent woman I’m not really sure what to do. The social norms on this topic vary case by case with men still insisting on paying for minimally the first date while respecting a woman’s ability to pay her own way.

My first foray into dating brought a gentleman who loved to bring flowers. He also loved cards. Although, we had some major incompatibilities this was very much appreciated. He could also sing like Frank Sinatra and would sing the song “Saying Something Stupid Like I Love You,” while twirling me around his kitchen in Los Angeles. I still have his cards, many of them funny, expressing his sentiments. He paid for most of our dates, but sometimes I would pay.

Another man was very formal. He would open doors, pull out chairs, and help me into my sweater. When he picked me up and I would forget my phone and need to go back into my house he would insist I wait for him to walk back around and open my door and we would go through the entire ritual again when I returned. Naturally, he refused to allow me to contribute to our dinner bills, although I did offer.

Since then I have been on many dates and awkward is the best way to describe the feeling when the bill arrives.

I’ve been avoiding making romantic decisions and moving forward with love until my daughters are both settled in college. I’m methodical in how I organize my life, so this is now an item placed firmly on my October to-do- list.

The preceding year and particularly this last summer has been devoted to my children. I’ve spent the summer watching the Bachelorette with them, going to dinner, and talking late into the night. We’ve had friends galore to our home, and assembled too many cheese boards to count.

I’ve been driving my older daughter to BART every morning and to keep things fair I often bring lunch to my daughter at the Orinda swim club where she works. Not just any lunch, but things like pesto chicken sandwiches and burritos from her favorite family run shop.

My daughters have been my number one priority since birth and I’ve never faltered in this. When I move my youngest daughter into her University dorm in late September this will no longer be the case. After that, I will be my number one priority and my own happiness will be the determining factor in any and all decisions I make.

When I married in 1994 I didn’t expect it to be much different from dating, but it was. We built our first house together creating a home and our love expanded. When we welcomed our first child into the world it doubled and then tripled when our second child arrived. When we moved to our traditional home near the park and grade school where we live today we opened our hearts to our new found friends and neighbors.

My older daughter called my relationship with her father Rom-Com from the start when he got on bended knee and proposed to me at the airport gate as I disembarked. We were very Felix and Oscar in personality in those days and as opposites attract we had a ton of fun together. I hope to feel like that again someday.

Until then, who picks up the check? And, how important is money in a relationship? Please comment with your thoughts below.

Love and blessings to all.

4 thoughts on “Money, Love & Dating

  1. In a true relationship based on Love, money should not become an issue between partners. Its simply a secondary means for expressing emotion. Getting gifts for your partner, going on dates, and things of such nature requires money. As long as its available, its not an issue in my world, and when its not available, life goes on. There are other uncountable ways bond stronger and keep happy. This is my humble personal opinion.


    1. Thank you for your comments. I believe money should not come between two people who are in love.


  2. Hi Sydney, I had to read your article because my father is involved with someone (understatement- they are engaged) and I’m finding that I resent the fact that she never pays for anything when we are all out together. He doesn’t resent it, but I have trouble with continually buying her dinner or paying for her lunch without any reciprocity. She is closer to my age than his, has a career, a college degree, a house and I am having trouble respecting her when she seems to be sponging off our family largesse. It’s probably time that I move on and try not to let this bother me, but I will say I’m not going to pick up the tab very often until I do. ♥️♥️Kim


    1. Dear Kim,
      This situation happens infrequently, but it is disheartening when generous people meet others that expect things, rather then appreciate them, and do not reciprocate. Even if you don’t have the resources to pick up dinner, flowers or a nice bottle of wine are always appreciated. I would be losing respect as well. Sydney


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this:
search previous next tag category expand menu location phone mail time cart zoom edit close