For each of the approximately one hundred first dates I have been on in my life, I can remember where I went. I sometimes can’t remember the guy’s name or what I wore, but I know what we did and similarly how much time I spent with him. After a man’s shining and sparkling self-declared strengths, the date is key. I don’t necessarily attach a great deal of meaning to where he takes me or obsess over what it might indicate about the future, but I do remember. Location sticks. It just does.
Too fancy, Too long
On Valentine’s Day my boyfriend took me to the District’s infamous Restaurant Nora. It is America’s first certified organic restaurant and has hosted many a D.C. dignitary including the President and First Lady. Everytime we passed I asked when he might be taking me there. It was likely quite annoying. But this Valentine’s Day, I got both a lovely dining experience and witnessed a brutal mistake.
The couple behind me was clearly on an early-stage date. I would guess it was their second or third date. He was sharing about his life: his first business venture, his daughter’s school troubles, where they grew up, etc. Stuff you would have already shared a month or two into a relationship. I rudely leaned back on the hind legs of my chair to hear more. Yep, confirmed second date. She looked overwhelmed. He kept talking and then there were weird silences. She would ask a question and he would fill in the space. Five courses equates to at least two hours trapped with your dining companion. I was happy to be with my long-term boyfriend. The woman behind me was not. In this, her date made two mistakes: too fancy and too long.
A too-fancy-date early in a relationship screams desperation. Sure women appreciate that an effort is being made on our behalf, but we also want something to look forward to. It feels uncomfortable to get something over-the-top before you know someone well enough. I had been dating my boyfriend for two years before we went to Restaurant Nora. He saved it. He made it special. While I might not recommend waiting two years, do wait. Taking a woman somewhere nice is sweet and thoughtful. Taking a woman somewhere that people who are married for thirty years celebrate their wedding anniversary is too much.
And too long! Five is a lot of courses to eat with someone you just met. No one likes to feel trapped with a person they don’t know. Even if the date is going well and you like each other, sometimes people just aren’t comfortable yet to share for three or four hours. I remember I went out with a guy who had drinks, dinner, a concert and a post-concert desert place planned for our first date. It was too much. For me, it removed the playful mystery that makes first and second and third dates so fun. I appreciate that he had a lot of ideas and was excited to spend time with me, but I didn’t need a six-hour date to prove that. I would rather get to know him over time.
Too casual, Too short
I don’t do lunch, coffee dates or just “a cocktail.” Some women do. I don’t. I want it to feel like an effort was made and, for me, meeting at Starbucks doesn’t feel like an effort at all. But even more tragically, both lunch dates and coffee dates are a prime set up for a good date to get cut off. The middle of the day is awkward because you don’t know when to leave or how to leave it, but you actually have to leave and go back to work. There isn’t enough time to create a strong rapport and for a mutual great time to materialize. Lunch signals that you don’t believe in yourself enough to think that I want to invest my time in you, or worse, you don’t want to invest your time in me.
I went out with a guy who suggested we go to lunch during a workday. I really wanted to go out with him, so I said yes. He made a reservation at popular midtown restaurant, and we had a nice lunch. Except that had it been dinner, I would have gone out for a cocktail or dessert or romantic walk along the river after. Being lunch, we had to rush back to the office and continue working. That is no fun! At work I cannot call all of my friends and tell them all about the date. Leaving someone after a lunch date is awkward. No woman wants a sweet first date kiss in broad daylight standing on the corner of 57th and 7th where your coworkers could walk by and see you. And for this date, I might have liked that.
I spoke with several guys who obsess over doing something “different” on a first date to stand out. I don’t think that’s a bad idea, but take it easy. Personally, I am a dinner and drink type of girl. I also live in a city where access to new places is unlimited. If your only choice is the neighborhood Applebee’s where you are certain to see everyone you know, then maybe dinner isn’t the best idea. Choose wisely, but don’t overthink it.
Women like to know that a man made effort on her behalf, but we don’t need everything over the top. It’s important to ask what we like to do or what food we like to eat. You don’t want to take a vegan to steakhouse. But at the same time, we don’t expect you to know everything about us. We don’t know everything about you. You don’t have to take us to our favorite concert or an art exhibit you know we would love. You don’t know us yet! The purpose of the date is to get to know one another.
The most impressive and heartfelt dates I’ve had are when the guy is his best self. He chooses a location where he feels confident and comfortable. In turn, I am confident and comfortable. We want your best self. If your best self is showing off your love for craft beers, take us there. If your best self is your neighborhood restaurant that is consistent and reliably good, go for it. We want the strongest and best you to come through. One of my favorite first dates was just a bottle of wine and a blanket in the middle of a fieldstaring at the stars. My date showed off his love for astronomy as we pondered the vastness of the universe while exchanging childhood stories. I still remember the constellations he taught me to identify in a summer sky. It was an unforgettable evening.
A genuine and heartfelt connection happens when you are genuine. You aren’t going to be genuine if you put yourself in an awkward position to impress a woman. We don’t expect you to take us to live performance art just because we said we like performance art. If you are going to feel like your best version of yourself watching naked people covered in paint running around a stage, then let’s go see some art! But if you really want us to remember you, chose a place where you will shine your brightest.
My commitment: to make this worth the read. Humorous, fun and introspective. I welcome your thoughts, ideas and feedback via email at firstname.lastname@example.org.