Someone famous once said, “Summer should be fun!” When it comes to summer dating though…that’s easier said than done. People are constantly going away or busy with fun summer activities, which makes it hard to actually see anyone you want to meet. This can lead to frustrating misalignments in time with people you’re convinced are your husband at first digital sight. Exhibit A: I still can’t believe I’m not married to the super hot finance bro I matched with in July 2015 on The League. While we were obviously perfect for each other, his being in the Hamptons/Mykonos for weeks on end while I was on Fire Island, upstate, and hiding from the 9th Ave Street Fair didn’t exactly bring us together. If only we matched in the fall!
Lately, though, I’m seeing summer as an opportunity to have some low stakes fun with a potentially outsized payoff. What a rare occasion! Everyone is tan and probably in a good mood and doing lots of fun things - let’s embrace that! It’s OK, and I would actually say a large and bright green flag, if someone’s life is so full when you meet them, such that you can’t see them again for a few weeks. While I used to think dating in the summer was a full wash for this reason, my new perspective is that it’s all upside, since you have nothing to lose but time. If you can’t beat them, join them. And maybe you’ll meet them while you’re out being generally fabulous, anyway.
So as we barrel towards MDW, here’s how I am approaching dating this summer. This is actually a bit of a New Rules moment - I think this is a valid four seasons approach to socializing, and will be my guide henceforth. That being said - no better time to launch than over a holiday weekend heralding the arrival of many people’s favorite time of the year!
Stop trying to date elusive people
No one is that elusive - they’re just trying to elude you. Accordingly, we will not be asking people to hang out multiple times when all they can give in response is a “I wish! I have all these plans that don’t involve you though!” According to most people’s Insta stories, it’s not that they don’t have time to hang, they just don’t have time for you. You don’t have to hate them for it, but it’s absolutely time to focus your attention elsewhere. Let them come to you if they want to. If they don’t…why would you want to see them?
Travel boyfriends
I hated travel bfs for a minute, but they’re definitely back. So if you’re going on a trip and none of your friends want to go with you and you’re single - we are asking the hot guy in New York if he wants to go. Who cares if it’s not going anywhere beyond an overseas moment? Those memories will last a lifetime.
Be too busy for your crush
“Hmm ok let me keep a night free so that I can potentially hang out with my latest crush if he’s free.” Ok, literal worst idea ever. No one is “holding space” for you without a duty to do so, so stop doing it for other people. Go away for a weekend and be generally unavailable during the week because you’re tired or maybe need to watch Selling the OC. Go to Europe and be unable to beat the “I feel like you’re always traveling” allegations. We’re saying yes to doing things we want to do, even if that pushes meeting your husband out a few months. I acknowledge I said stop trying to date elusive people - you can do both! Reach out if and when you have time, and then stop if they aren’t reciprocating. It’s called burden shifting.
Embrace being single
Too many of these people in relationships hate their boyfriends. Stop feeling inferior to them! Be happy that you get to do whatever you want do, when you want to do it, if you want to do it. Not everyone has that, to their credit!

Flirt with people while on a date with someone else
If I am on a date and we run into a third party who 1. I think is cute and 2. Is flirting with me, I will absolutely be flirting back with him. A little competition never hurt nobody. Also, if I don’t flirt with this my, my date is going to. Takeaway: if you see me on the beach with someone you think I am dating, approach me anyway.
No elaborate dates
If I want to go on a date with someone - I’m gonna say “Let’s hang out.” If they say yes then I will suggest doing something that I want to do, and that something is going to be simple. I’m in the mood to go to the Olive Garden? We’re getting soup/salad/breadsticks. I need to go to Costco? He’s coming to buy a rotiss with me. Starbucks moments after leg day at MM? They’re incoming. No more scouring Resy or going to a concert or trying to be chic at some god awful hotel bar in WeHo. The name of the game is easy and I will not be wasting any more bandwidth on crafting some cute date. You can though!
The timeline is getting a little thirsty
If you look really good in that picture, go post it immediately, or maybe wait til tomorrow morning. If you just had something really good happen at work, you’re telling everybody about it. I don’t care about seeming humble anymore because no one else seems to, and at least in LA, you’re punished for it.

Cut bait immediately
Do you feel like your latest crush is acting weird all of a sudden? Did they leave you on read, or worse, hit you with a “Sorry just seeing this?” You know what Bethenny, we are done. When your gut is telling you something is over, let’s assume you’re right and pull back; let the other person prove you wrong. This means no more likes or DMs and absolutely no texts. Stop giving them any attention at all, as they can give you some for a minute. Without pushing them away, we will be guided by the principle that “If they wanna see you, they will come to you.”
Lean into awkward silences
If your date is a bad conversationalist, do not pick up their slack and try and fill the void. Sit there and be uncomfortable with them because it’s not your fault they can’t hold a conversation. If it gets awkward enough - leave! I am so over the headaches resulting from doing all the talking on bad dates. Plus if you have no chemistry on date one you will never have chemistry!

Play games right back
The high road is now closed and it’s your duty to play games right back when someone else starts. They consistently wait 4+ hours before responding to a text? You’re now waiting at least 8. They’re 20 mins late to your date? You suddenly have to leave 30 mins after they arrived. They always say how hot you are but have literally never asked you out? You’re deleting the text chain with their unsaved number and saying “Hey who is this?” next time they resurface. People know what they’re doing and when they treat you poorly, you can either tolerate it or send them a message in return. This feels a little childish, sure, but it also feels really good.
Casually get to know someone before going on a date
The proper order is: Get to know someone a little bit —> Go on a date. This could mean some flirty and lightly substantive text convos, a hookup, or a moment at a house party or bar where maybe you make out for a second. I will not be going on dates with total strangers anymore (why did I ever?) because I simply refuse to show up and discover I have absolutely no interest in someone within 60 seconds of sitting down. That of course can still happen, but we will be mitigating that risk to the extent we can.
And finally…
Be direct
Do you think someone is cute and you can’t tell if they just want to be friends? Are you so strongly attracted to someone that all you can think about in the moment is [redacted] them? Tell them! There is no shame in being into someone - and if the extent of your desire exceeds the extent of theirs, all that you risk is a slight ego hit by revealing yours. The reward? You get to move on and find someone else! Or even better, maybe they’re into you too! Don’t be scared to say exactly what you want - especially if it’s regarding me.
So have fun dating around this summer! It’s all upside and really is not that deep. And remember - if you see me on a date, come and flirt with me.