So, this past weekend we hosted your wedding. It wasn’t our intention, but you and your friend Shiloh were so into the idea of getting married that her mother finally called and said, “I think we’re going to have to do this thing.” Once confirming that the bride and groom both understood it was, in fact, a (said in a whisper) “pretend” wedding, the parents got to planning. The thing about me and your Dad (and, as it turns out, the bride’s parents) is that we can’t do something at 70%. A wedding to you guys basically consisted of fancy clothes, an aisle, vows and cake – with cake being the big draw. The adults added flowers, snacks, a decorated venue, ring pop favors and, thanks to Shiloh’s mom’s job, a limo – so guests under 5 could drive around the block for 20 minutes. Ridiculous? Maybe. Super fun playdate with a theme? Definitely. When I asked the flower guy at the grocery store if I could have any roses they were going to throw away, he asked me what they were for. I said I wanted to use the petals to decorate a 4-year-old wedding. He said, “For someone who’s been married 4 years?” and I said, “No, for a wedding of 4-year-olds.” He looked at me like I was cracked. I explained that everyone involved knew it was just for fun. But this morning when you told me that, now that you’re married, you and Shiloh would be “getting an apartment”, I wasn’t so sure. I said, “You’re not getting an apartment. You’re staying here with me. You know you’re not really married right?” You looked at me like, duh… and said, “I knooooow Mommy. But when I really marry Shiloh one day, we’ll get an apartment.” I said, “I hope you get one before that.”
The thing is, if you grow up and marry Shiloh, that would be fantastic. She’s a darling girl and we love her family. Plus, telling people you got married for the first time at 4, would be pretty hilarious. But, you don’t know who the heck you’re going to marry, and I’d hate you to rush headlong to the finish line of relationships before exploring the whole exciting gamut of love and dating. As I’ve said before, I love being married and I’d love it for you, but there are so many wonderful things to happen between now and then. Don’t miss out by trying to achieve the end result.
Your Dad was a long-term-relationship guy, and judging by your adoration of the female sex – your penchant for complimenting women, and the fact that you notice things like when I’ve had my hair or nails done – you might be too. I, on the other hand, dated a lot, and had only a handful of real relationships before I met your Dad. That was good too. I’d hazard to say I probably had more fun than your Dad, but I also had more heartbreak, so it’s a toss up to which is better. I’d like to see you have a lot of experiences. To date women that aren’t right for you, and women you think are, but turn out not to be. I’d rather you to go all in, and feel the crushing sting of a failed relationship, than hang back and choose the safe or easy path. Love in itself is a risk but it’s a risk worth taking over and over again.
As you start your dating adventures I have a couple words of advice. Keep in mind I was a pretty avid dater in my time and I ended up with a great spouse, so I kind of know what I’m talking about. Plus, I’m a woman, and that gives me some insight you wouldn’t otherwise be privy to.
Try not to have a “type”. I can’t speak to who you should be attracted, that’s just chemistry, but try to avoid limiting yourself to a certain hair color or look. Avoid saying things like, “I don’t date (fill in the blank) type of girls.” You never know where you’ll make a connection, and if you close those doors without finding out what’s behind them, you might be missing out on a great love affair – or at least a great story.
When asking a girl out, be direct. Decide what you want to do- go to a dance, a movie, dinner – and man up and ask. You can be casual, “We should go out sometime” or “I’d like to take you out this weekend. You interested?” “Are you going the dance?” Yes? “Great. You want to go with me?” I’m not sure? “Well you should. Let me take you.” Or something like, “I want to check out this new restaurant/band/movie, you wanna go?” I can’t promise everyone will say yes. Keep in mind what I said about regrets, the ones that say no often do it for reasons that have nothing to do with you whatsoever, but at the very least she’ll be flattered and impressed by your confidence. Just be sure you’re clear with your intentions. You go further being bold. You don’t want people to say, I think he was asking me out…
Oh, and a smile never hurts.
My first date was with a boy named Andrew Westlake. I was 9 or 10 and he asked me to the movies. His mother drove us to the theatre and sat behind us with his little brother. I remember his brother teasing us and Andrew freaking out. I remember chocolate covered raisins. I remember his mom trying to give us some privacy by not talking to us. But mostly I remember feeling special.
Make your dates feel special. Pay attention to what they say and act like a gentleman. It’s always nice to start with a sincere compliment. Not random, placating niceties, as they come off as shallow and calculated, but something you believe to be true and say out loud. “You look really pretty”. Or, “Those jeans look awesome”. You want to be candid and genuine. Trust me, girls know the difference. Plus, I guarantee she put some serious energy into how she looks. Acknowledge the result. It’ll make her more confident, which makes her more comfortable, which ultimately makes the date more successful.
A successful date is one where the conversation is easy, the company is good, and the time just flys by. If the physical attraction is there too, then you’re golden. Sometimes you’ll find yourself on a date with someone you found physically attractive, but once you’re out with them, it’s kinda tough. I dated an investment banker in New York once who was handsome, smart, romantic, and had a ridiculously enormous 2 floor apartment that I hosted a number of parties at (trust me, that was a big deal). Sadly, we just didn’t click.
One winter night, we were walking through a beautiful, empty, East Village park. The trees had ice on every branch so they sparkled in the lamp light, the ground was lightly dusted with snow, and there was a slight mist, so everything just seemed magical. I commented on the beauty and asked if he had to choose a way to describe it, what way would he choose? When he looked at me with consternation, I elaborated. Take a photo? Write a poem? Draw a picture? His face was blank, and he said something like, “Why would I want to do that?” I let it go, but in that moment, I knew we were over. Zero. Imagination.
That’s the thing, someone can be good on paper, and not right for you in real life. When I first moved to LA, I met a guy on Halloween. I was, if you can stand it, at the Playboy Party – sadly, not at the Mansion. I met a guy dressed in a full superhero costume. Afro wig. Tights. Mask. The whole deal. He was pretty funny so I gave him my number. We talked a couple of times on the phone and then met for a date. This sounds ridiculous, but when I saw him again, out of costume, I was disappointed.
I was disappointed not because he was unattractive, but because he was too attractive. Too chiseled. To generically handsome. I guess I’d gotten it into my head that he was this quirky dude, and this guy was not what I expected. But I thought to myself, Really Leigh? He’s too handsome?! Get a grip! At dinner I found out he was not only an ex-fighter pilot for the air force, but a Harvard Grad who lived at the beach and worked for a Hedge Fund. He had a motorcycle and took weekend trips to Palm Springs and Vegas. On paper he was perfect. In real life, I wasn’t sure if I was attracted to him. For our second date he invited me to a BBQ at a friend’s house. I drove to his place in Manhatten Beach thinking, Ok, this might be something… When I got there his house at the beach turned out to be a glorified frat he shared with multiple buddies. It was the kind of place you’d be afraid to walk barefoot or use the bathroom, not the place of a 30-something man. I was happy to leave it to go grocery shopping, until we got to the store and he was all, “Babe this” and “Hon, that”. “Grab the mustard, kay babe?” When did we become a long term couple? We’d skipped like 15 steps. By the time we got to his friend’s, he was acting like he couldn’t wait for our wedding and I was weirded out. When he got hammered and hit me with a “You can drive, right babe?”, I was done. On paper can be deceiving. I thought I could ignore the lack of chemistry by focusing on his credentials and, subsequently, looking at me on paper, he thought he could just plop me into the girlfriend box. It doesn’t work that way. When he leaned in to kiss me that night, I put my hand in front of my face and high fived him. I think I actually said, “High Five!” It was pretty awkward. I never saw him again.
As a general rule, I think men should pay on a date. I know we’re liberated and all that, but I’d advise you to still pick up the tab. It’s old school, but classy, and chicks dig it. Don’t go broke dating a girl, or try to impress her with expensive places or gifts. Sometimes too fancy/expensive is a turn off in itself. It comes off as needy. Thoughtful gifts almost always trump pricey ones, and if you don’t have the cash don’t pretend you do. Just don’t be stingy with your attention or your wallet. Cheap is unattractive.
Consider your date’s interests. See what she likes before making plans. Never show up with the thoughtless, “I don’t know. What do you want to do?” Take charge. Just be sure not to push or try too hard. I dated a guy that always had to plan a big thing. A grand gesture. Going to see Rent and then going to the top of the Empire State Building. Tour of the Hudson on a riverboat and then dinner at some swanky place. He was more into showing off than getting to know me. I told him I wasn’t ready to be committed. I was. I just wasn’t ready to be committed to him.
Don’t get wasted on a date. At least not alone. If you’re out having a ball and you’re both buzzed, fine. Just don’t get sloppy (try and avoid this whether you’re on a date or not). Don’t get her wasted to make things easier. It’s obvious and weak. Earn the action you want, don’t try and trick her into it.
I went to the movies with a guy in Montreal once who hadn’t bothered to check the times, so we were an hour and a half early. We went to a pub and he proceeded to order 6 shots of tequila. I didn’t want tequila but he didn’t care. I did one shot, to placate him and stop the barrage of “Don’t be a pussy“, and he did the other 5. He proceeded to get in a fight with a guy he claimed owed him money, made me write down the guy’s contact information, and ordered and drank 3 more beers. During the film he kept trying to grope me, and when the movie was over he ended up screaming at me on the street because I’d had the audacity to hold the door for him. His arm was in a sling from a rugby injury and, in his mind, I was trying to emasculate him by treating him like an invalid. I told him he wasn’t an invalid, he was an idiot. I never saw him again either.
Be on time. This is a good rule for life. Promptness is both appreciated and respected. I wasn’t so great with being on time growing up, so I’m putting more emphasis on it now. If you’re going to be late, let the other person know. There is no excuse for not doing it in the cell phone age. And if you are late, for goodness sakes, apologize. I once went on a date with a guy I’d met shooting a deep sea fishing television pilot. (Don’t ask) I was one of the only people that didn’t barf on the very rough sea. For this reason, and this reason alone, I came off as more attractive than my model costar. All 5’10” of her Swedish body was literally green. My future date was a friend of the producer financing the shoot. We made plans to meet for dinner at a little Italian place in the West Village. I ended up sitting at a table in the window for 45 minutes drinking alone. No call. No text. Nothing. I was about to leave when he breezed though the door without the least bit of contrition. Everything in my body said, Get up. Go. Leave him with the bill. I wanted to say something cool like, “Ok, I’m glad you’re alive. I had too Pinot’s. Be sure to pay the man.” But did I do that? No. I let him talk me into staying for dinner where he proceeded to talk about himself for the whole evening. I knew I was better off not to return his calls after that.
If you’re on a date that isn’t working out, see it to the end, and then exit as politely as you can. Don’t extend it. Don’t go for drinks. Don’t say you’ll call. Be kind and hit the road. If it’s just unbearably terrible – she’s a fall down drunk, or a racist, or crazy – then call a spade a spade and excuse yourself. “This isn’t really working out. I think we should call it a night.”
If you’re ending more than a date, do it with grace and class. Don’t use social media. Don’t have a friend do it. My first boyfriend – and I use the term loosely as I’m not sure if we were ever alone in the same room – had his best friend tell me he wanted to end it. Even as a 12-year-old I knew that was lame. At minimum, make the call yourself. In person’s better, but not without mess. My boyfriend from first year theatre school blindsided me with a a breakup in Central Park and I lost it. I acted like a crazy woman. I stumbled out of the park in a haze of tears. I’m sure the people on the subway thought someone had died. In my defense, I was in a pretty dramatic phase in my life and that breakup was a culmination of many bad breakups, so my reaction was a bit extreme. I was also devastated because he gave me no reason. It was just over.
Always try and give a reason. One she can learn from like “This is just too intense”. You’re basically saying, “You’re too intense” but in a way she can process and maybe learn from. Or give her one she can move on from like, “I don’t want to be in something serious right now” or “I have to concentrate on my work”. She’ll be sad but she can feel it wasn’t her, and she can’t fix it or change your mind because it’s not up for negotiation. Just be compassionate. Being dumped hurts like hell. Do it as nicely as possible, just make sure you do it. I dated a guy for 2 months that literally left my apartment one morning and just stopped talking to me. Nothing had happened. It was just as if we’d never met. At least, by that time in my life, I had the foresight to tell him off when I ran into him on the street months later. I was calm and concise. I told him he handled what had happened with us ‘badly’. I said next time he shouldn’t be such a coward, and just have the balls to tell the girl it’s over instead of just running away. His mouth was hanging open as I walked away. It was a great moment.
If you’re the one getting dumped – and I’m sorry you are – it’s the same thing. Have dignity, class and balls. Never argue or debate their decision. It’s made. Challenging it only makes you look desperate and doesn’t improve your chances of getting back together, if that’s what you want. My first boyfriend in NY dumped me out of the blue after we’d seen each other, at his insistence, every day for 3 months straight. He’d invited me away for the weekend to meet his mom, but I had to work. When he got back he told me he “needed space”. I acted cool, like it was totally normal that he’d asked to go away to meet his mother and now wasn’t sure if we should be together. When we had lunch about a week later, I brought him a postcard of the Grand Canyon. I thought I was being light and funny. That’s space isn’t it? But it was already over. I’m glad I acted cool, but I regret not asking some questions. What had changed? Why was he doing this? It wouldn’t have altered the outcome but I could have saved me months of wondering.
If you’re in a relationship enjoy it. Who cares if your friends ride you for being AWOL for a while. They’ll get you back eventually. Relationships, especially new relationships, are so exciting. Being wrapped up in love is the best. Just remember there’s a whole world out there, and once you surface from the initial haze, broaden your horizons.
If you get to a point in the relationship that you feel like straying, have the courtesy to break up with her first. I only cheated on one boyfriend. I knew it wasn’t going to work out long term, and when I met this other guy, I thought I’d see where it went before I made any changes. Essentially, I hedged my bets. My boyfriend was away most weekends so I started casually dating the other to see if it was something worth breaking up for. The affair imploded – as things tend to do when you’re not being honest – and I stayed with my boyfriend for another 3 months, but it was never the same. I had one foot out the door and should have just ended it when my affections had strayed. It doesn’t work out much better when you’re the “cheatee”. I’ve been the ‘other woman’ a couple of times and it’s sexy for a moment, and then it’s just depressing. One guy’s girlfriend lived across the country and we’d never met. As far as I was concerned she didn’t exist. But it was almost as if he was just filling his time with me till he could be with her. It made me feel used and shi**y. The other time I thought I’d found my soul mate our connection was so strong. I truly believed he’d leave her for me. He did leave her, but for one of the other girls he was fooling around with. I was heartbroken…and stupid. Affairs only lead to pain. In the world of dating if you find yourself about to cheat, hold off. It’s much more fun if you’re both available. Maybe not as sexy, secrets can be hot, but definitely more worthwhile.
One last note on cheating: I’m of the belief that if you cheat, it’s on you. You’re the one who screwed up, so you should be the one to suffer. People confess to alleviate their own guilt, but it only serves to hurt the person who did nothing wrong and doesn’t deserve the pain. Don’t rub your dalliance in their face. If you cheat or want to cheat, accept the obvious – the relationship is probably over – and be mature enough to end it. In a long term relationship like a marriage, my opinions on this issue are slightly less cut and dry. But sufficed to say, I’m anti-cheating.
When dating be confident. No girl wants a guy she can push around. Flexible, but not whipped. Girls like puppy dogs but they don’t respect them. Be honest with what you like – food, movies, people, interests – but also about how you feel – regarding issues, behavior, and feelings. Be yourself. Have, and be proud of, your opinions and if she doesn’t get you, f*$# her. Her loss.
Dating and love are exciting. Sometimes painful, but for the most part pretty awesome. Every new person teaches you something about what you want, and what you don’t want. What you need, and what you like. What works for you, and what doesn’t. When I finally found your Dad, it was easy for me to get married. I’d done single, and I’d done it well. I didn’t need to wonder what else was out there or if I was doing the right thing. I knew. I knew because I’d done the work. I knew the landscape and I could say with all certainty this was a good plan. I believe it can work if you marry young, or marry your high school/college sweetheart, I just think it’s those couples who are more likely to wonder what they missed, or be the ones pining for the things they never got to do. I got to do them. It was fun. It was painful. It was wild, and then it was over. On the first date with your Dad I turned the page and understood that one chapter was closed, and another one was beginning. And I was ready.
Enjoy the ride until you’re ready.
I love you.
xo your mama