10 Rules to Being a Gentlemanly Date

Given the number of strange encounters I’ve had when dating in SF, I felt the need to write this to weed out the weirdos.

1. DO COURT ME. If you ask me out, you should pay for the date. If you ask me to split the bill, there will not be a follow-on date. It’s one thing to divide up costs according to earnings when you’re in a committed relationship- But if we’re just dating, I still haven’t decided if I like you yet. Trust, affection, and a true friendship are built over time and earned through repeated acts of compassion. Would I ever ask or even let you pay for my bills? Absolutely not. Anyone who knows me understands that I’m more than capable of taking care of myself and I’m far too impatient to date someone just for a free meal; But I don’t feel the need to seek your validation by throwing my independent nature in your face. I want to know that you’re going to invest in me and not take for granted the many ways in which I would invest in you, and courting me is a big part of showing me that you value me. If you’re transactional about your money, you’re going to be transactional with your love. Numerous studies have shown that the key component in a lasting relationship is generosity. I am generous with my affection in many different ways and invest a lot into the person I’m seeing. You picking up the tab when we go out makes me feel like a lady, and makes me feel like you value me. If you have an issue with this, consider that I don’t make you split the cost of the makeup, new dress, shoes, etc. that I purchase for the date 😉 Put your best foot forward to win my confidence by manning up and grabbing the check when we’re in the dating phase.
2. DO HAVE CONVICTION. If you think that dating is like Salesforce or you’re trying to get the most ROI out of the least amount of effort imparted, then I can guarantee that we’re not a good fit for each other. I’m not into transactional relationships and I don’t need you in my life; But if I really enjoy you as a person, I will put a lot of effort into figuring out how to make things work. If you don’t appreciate that and are looking to play the numbers game, just go away and leave me to live my already awesome life in peace. And if you’re convinced that I’m the real deal, then put in the necessary thought and effort: Be creative and plan ahead. Your actions speak louder than words.
3. DO PUT IN EFFORT. It doesn’t take a lot of money to have a great date, but don’t consistently be a cheap ass if you don’t need to be. A surprise picnic with bubbles in the park or a dinner made by you are just as charming, if not more so, than an expensive dinner out. It shows that you took a lot of effort without you having to dish out the dough. And if you’re truly in a pickle financially, be honest, tell me, and let’s get more creative with planning. It doesn’t matter to me as long as I feel like you’re putting in effort.
4. DON’T TRY TO GET ME DRUNK. While I can drink like a horse, I don’t want to feel like crap tomorrow. Ask me to dinner, not to drinks. Eating good food is the #1 thing that makes me happy! And I’d rather experience a new cuisine with you than get drunk. Drinks are okay for date #1 when you’ve yet know if I’m a horrible person or not, but not after that. And definitely don’t ask me to coffee- This is not a business meeting. (And I don’t drink coffee.)
5. DO RESPECT MY TIME. I’m a busy person too, and am generally booked up a week in advance, sometimes 2-3 if work is crazy. Don’t expect me to be free last minute, and don’t ask me to hangout with you late at night or on the day of. I’m not your booty call.
6. DO RESPECT MY BOUNDARIES. Take the time to get to know me as a human being first, before you try to decide if we’re meant to be or not. Don’t expect me to welcome you into my apartment or spill my life-story to you within the first few dates. I won’t expect to know you off the bat, but I will make a big effort to understand and learn about you. Don’t be presumptuous or pushy if we’ve only been on a few dates- It takes time to get to know someone and for me to feel comfortable with letting my guard down. If you’re looking for instant gratification, go hit up the Battery on a Thursday night instead. Also, never order for me! You are taking away my greatest joy in life when you order on my behalf. And considering that I probably know more about gastronomy than you do, why in the world would I trust you to make the decision that gives me the most joy in my life? It’s one thing if I ask you for your suggestions, and it’s another to presume that you know what I want to eat or drink. Cardinal sin, my friend.
7. DON’T BE A MORON. I can’t stand people who have a herd-mentality, are poorly thought-out, or simply haven’t done their research. I certainly don’t mind opinionated viewpoints, as I have many of my own, but you’d better be able to back them up while still bearing an open mind and eagerness to learn. I can smell bullshit a mile away- Don’t think I won’t call you out on it directly. If you want to go out with me, you’d better be an intellectually apt conversationalist, and have a zest for life. Otherwise I’d rather eat by myself.
8. DO MAKE THE LITTLE THINGS MATTER. I am old-fashioned and I was raised with certain standards, etiquette, and a sense of common courtesy. I’ll be polite and take the time to look nice for our date. I appreciate when a man opens doors, pulls out chairs, stands on the car-side of the street, etc. If you want me to act like a lady, make me feel like one. Also- Do not be on your phone during the date- If it’s an emergency, be apologetic and excuse yourself from the table.
9. DO BE CLEAR ON WHAT YOU WANT. Be clear on what you want out of your life and who you want to engage with. The ‘who’ matters more to me than the ‘what’- I don’t care particularly to jump into labels, timelines, etc. but I do care about who I’m spending time with, and that the person values me. I also care that the person I’m seeing isn’t afraid to fall in love with me. If you’re like the other 99% of men out in SF who are waiting to get their $100M exits before emotionally investing in anyone else, then do me a favor and leave me alone. I don’t want to date someone who’s biggest fear is falling in love.
10. DO LET IT BE ORGANIC. Chemistry is the biggest determining factor of whether or not this is working- Enjoy our time together and be present! (Yes, this means putting your phone away!!!) Don’t try to make things fit in a certain mold, or have unnecessary or premature conversations- Just let it flow.