Ask Lauren: My Best Date Ever


Ask Lauren: My Best Date Ever

I love when I have the chance to answer your questions in my Ask Lauren posts. Today’s question came from a private message that was sent to me. It’s a fun one, so I thought I’d share my answer with everyone. Here it goes…

Hi Lauren! What is the best date you have ever been on? I am looking for fun date ideas to go on with my guy. We have been dating for almost two years, and I am all out of ideas.

While I’ve shared quite a few fun date ideas on the site before, the truth is that my best date ever wasn’t super adventurous or creative. It was my second date with my fiancé William. On our first date, I was so nervous that I couldn’t really enjoy myself! But when he asked me on date No. 2, I was feeling a little more relaxed. William wanted to go to a bar to grab a drink together, but I had lost my I.D. and just sent my passport away for my trip to Africa for The Little Market (I know, smooth move…). So, since we couldn’t go to an actual bar, we went to a hotel lobby bar and played cards all night. We literally closed the place down, just playing cards, talking, and laughing. And nevermind the fact that I lost… I actually kind of liked that William didn’t just let me win!

I knew he was a keeper after that night. While it’s fun to spice things up with new activities and adventures, I think that a sign of a strong relationship is when you can have fun doing even the simplest activities together. That’s still true of William and I to this day.

Do you agree that sometimes the simplest dates are the most fun? What is the best date you’ve ever been on?

Share in the comments below.

XO Lauren

Photo: Lauren Conrad Style
Categories: Ask Lauren, Contributors, Grow, Lauren Conrad, Relationships
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  • JJ

    you’re my idol Lauren and I’m glad you’re happy, it give me hope tbh! and yes the simplest dates where you talk all night hen cuddle are the absolute best <3

  • Sevda K.

    I think it has a lot more meaning when everyday activities become something special just because you are doing them with your s.o.
    If it is meant to last that is the way it should be. Hope that you stay this happy and I wish you two all the best!
    XO Sevda

  • Alyssa J Freitas

    I love going on a picnic for a date! It’s so nice to just relax and enjoy the weather. I always bring card games and a ball for catch to make it fun.

    Alyssa | Keep It Simple

  • Grace

    Aw, this is such a cute post! I love when you share personal stories and tips! Congrats again on your engagement to William…just thought I’d say it one more time haha :)

  • Yazmin

    That’s so cute! Now I just need to find me a guy to have simple dates with…

  • Alanah.k

    A late night game of battleship on the patio. We have been together 6 years!

  • Melissa Nelson

    My favorite dates with my guy is when we go to the most adorable (and my favorite) coffee place in our downtown. We can literally spend hours talking and laughing over a nice latte:)

  • Nathalia Kalil

    That is a cute love story! I think we know when the guy is the right guy! :)


  • arielle q.

    love your answer for this question! and I would have never thought of that…playing cards in a hotel lobby bar. but it does sound super chill and relaxed! no wonder you two are such a cute couple.

    love, arielle
    a simple elegance

  • Nikita

    How do I ask Lauren a question? I’ve searched all over the website and can’t find it. Someone help me please!

  • Stacy

    Yes the simplest dates can be just as fun. My favorite dates have also been just the time being together and getting to know each other. Anything with food is a great way to bond too!


    Well…my boyfriend and I try to go every weekend to a nice Restaurat, and i think that its a way to talk about your week and share some drinks….always is romantic to go some place to remember your fist date or your first kiss with him

  • nailyoubackup

    My favorite date with my boyfriend of 4 years was a bike ride. We decided to take out the bikes for the first time this summer. We originally wanted to drive 30+ min away but realized it was too hot and no shades on the paths so we stayed closer to home. Which was perfect because the bike that I had was close to falling apart so we picked up a new one we saw earlier in the day, which wouldn’t have happened if we drove the 30 mins. away. After that was settled, we took a scenic ride around his childhood neighborhood, which was starting to have cute little shops pop up everywhere. Then towards the tail end of our bike ride, we ran into a small local jazz festival in the park. We got to see a lot of local artists and doggies running around everywhere. When we were biking away from that, laughing about how awesome it was we ran into that, we saw a carnival going on in the distance. At this point, we were like little kids again. We split a funnel cake and people watched. Then we walked along the beach to look at all the amazing kites being flown. Ended our date walking towards the end of the pier right when the sun was setting. It’s my favorite date thus far because absolutely NOTHING was planned and it still ended up being perfectly dreamy.

    • LydiaGrace

      It’s one of the best things I’ve read all day!

      • Samantha Brown

        I agree!! I think anything that makes you feel like you’re a little kid again is always going to be good! And planning things out so much can kill so much of the fun – when you have no plan you’re open to so many amazing things (with this lovely story as proof). Thanks for sharing!

        Sam xx – how to make the most of your twenties

  • Emily
  • Christina Richards

    my boyfriend and i bonded over playing egyptian war (a very fun slapping game, haha). simple dates are the best.

    – christina

  • Ashley of Dream.Live.Repeat.

    I think you’re absolutely right about that date being a sign of a great relationship!! My guy and I are similar to you two in that way! :)

  • The Single Diaries

    That’s great! Thanks for reminding all of us that the best dates are ones that feel effortless.


  • Brittany Williams Martin

    The best dates are ones at home! I always thought that after we got married, I would miss going out all the time, but a night in really is so relaxing and fun!


  • Sarah

    My favorite date with my husband was our 3 year wedding anniversary. We went out to dinner at Olive Garden, then he took me to this place called The Track where he took me on my first go-kart ride and then we spent two hours playing games together in the arcade. We felt like teenagers on a date and we loved every minute of it.

  • Dani Kreeft

    Agreed! One of my favourite memories with a boyfriend is climbing onto the roof top of my old apartment building and just chatting straight into the night. Sitting and talking, no bells, no whistles. It was the best.

  • Jessica

    That’s so sweet, thank you for sharing! I’m happy to see that something so sweet and simple as a date you had made you happy and comfortable. Can’t wait to experience my first fun date!

  • Laura Jane Atelier

    I agree:) Sounds like you found a good one.

  • GL

    My favorite date has to be my first ever “first” date with my boyfriend. I’d never formally been on a date prior to this one. He took me to Arazmendi Bakery in the Mission District of SF. We couldn’t find a table so we ordered two slices of pizza and sat outside by the sidewalk. We must’ve sat there for hours talking, learning about each other. We stayed out until just before midnight (orginally meeting him at 3pm). Making every excuse to stay out, next dessert, next coffee, until everything was closed and were forced to part ways. We’ve been together for almost 2 years now and everyday feels like that first one.

  • Leanne

    That’s so sweet!!! Sounds like the perfect date!

    Love from South Africa

  • Tracy

    A great post, it has made my day!

  • Tay

    My favourite date was a totally spontaneous one! I had finished an appointment early and he had the afternoon off so we decided to grab a bite to eat, drove around for 10 minutes and found a hidden cafe, then went for a drive and ended up in a beautiful park where we watched ducks in a pond and ended up hiring bikes and watching the sun set :) it was the best date because it was unplanned, and totally spontaneous! :)

  • gulsah

    my favorite date with my boyfriend was first one.we decided to go movie.we are too shy.he said that his friends was in the movie.i accepted.but movie is too funny to first was teddy bear…
    he bought some popcorn and icetea.when i was drink the icetea i spilled on him.cause film was crazy.i was too nervous.but he said that is not problem.we laughed too.and i touched his chest first time.i controlled he was cold or not.because my icetea was too cold.he said to me calm down.his eyes, smell i didnt forget.we haved fun together.funny thing is we are broke right now.first love is unforgotten

  • Tom Sproull

    Spur of the moments dates, totally unplanned, are the best! A stroll by a waterfall or getting homemade ice cream for dinner unexpectedly, or finding yourself in a fun shop and buying your someone special a fun gift, those are the best moments!

  • Tatiana

    My best date was my second one with my boyfriend too! He took me to the mountains to teach me snowboarding. It was so much fun to do something active together, it was totally out of my comfort zone so I was completely reliant on him, and it made me completely let my guard down – no one looks good the first time they snowboard! After having him pick me up off the floor for the 50th time I realised his patience was endless, and that we had no problem laughing at and with each other.
    Afterwards we went to a tiny restaurant full of wood and roaring fires and I fell for him over a pungent bowl of garlic soup. We go back there every year to celebrate our anniversary.

  • Elle

    Love this story!

  • Alex

    I just asked my boyfriend about this after reading your answer, and we agreed on the same date. On our third date, I had a similar situation (forgot my purse and id at work, 45 minutes away from my house). We were planning to go play bingo at a local bar, but could not because of the id situation. We ended up going bowling at this very run-down bowling alley by my house. He then drove me the 45 minutes back to work to pick up my stuff. I am a teacher, so I showed him around my school and classroom. We then grabbed dinner. We were having so much fun that we then grabbed drinks at a local establishment close to my house. In total, it was a nine-hour date! Definitely memorable :)

  • Jamie G @ SnapGinger

    My favorite date was during a trip to Sedona last year- it was a quiet Wednesday night, and we had a great dinner at the restaurant in our hotel, we sat at the bar and ordered a half priced bottle of wine and then played backgammon and pool for hours! Just laughing and having a ball.

  • Ashley Marfori Lutton

    Since we are married and just starting out in our careers, the less money we spend on a date the more we can enjoy ourselves.

  • Sarah

    I have always wanted some guy to take me on a date that would blow me away by the romantic-ness of it all….but then after date after date with guys I realized that sometimes you have to stop wanting and let things surprise you, my grandpa always said put want in one hand and your shit in the other and see which one fills up quicker…….So , Surprisingly I met this guy in a Wal-Mart parking lot..he asked if I wanted to go out sometime and even more surprisingly I said yes…then when he did take me out he brought a car packed with water bottles, a blanket and a really nice lunch and I thought ohhhh a picnic nice, and asked about it….right away he told me he was not going to give anything away and that we were going on an adventure. I was a little stunned…but we went to a spot where we pulled off the side of the road and im thinking..creeeeepyyy….but after turning my phone on loud and making sure it was in my hand at all times….we went on a trail off near the side. after a short and very comfortable hike we ended up at a waterfall that in all my years of living in the area never had a clue existed, never even knew we had any within 100 miles and we set up and had lunch. He had made it himself, and it was delicious. After he asked if I wanted to put my feet in, so we did and he held my hand and told me I was the most beautiful and special girl he had ever met..

    Two years later and we are dating for the purpose of marriage.. Never thought I could be this happy and never thought I would find all the romance I needed from a hot guy in a Wally world parking lot….

    Amazing how that goes. Live life ladies and focus on yourself, the right guy will come along.

  • Lila

    Hi Girls,
    I cannot believe I am going to ask this here, but this article just pops up at a weird moment in my life.
    I am 23, but never really been in a relationship or been on a lot of dates. I met a guy a few weeks ago, and we’ve been on four dates. Things were going pretty well, until last weekend. We weren’t supposed to see each other cuz I was out of town for the weekend, but due to work I changed my tickets at the last minute…
    I told him “hey, I’m in town this friday night, what about drinks together?” I got a reply saying “Haha I don’t know, we’ll see”, to which I just said “Ok, let me know”
    It’s been four days, and no news ever since….
    What do you guys think?

    PS: sorry if I made mistakes in grammar or something, I am French and English is not my first language :)

    • Melanie

      If he wants to see you, he will make it happen or at least reschedule if he already made plans. And if he doesn’t, he’s not worth it. I also didn’t have my first boyfriend until I was in my twenties but from experience I can say that if there are signs early on that you are not a priority then save yourself the heart break…Being patient is soooo worth it! Good luck lady!

  • Lexarod

    Wow great date thanks for answering …yeah love you blog

  • FernandaR

    I couldnt agree more..when you can have a good time just playing videogames or watching a movie and staying home, you know you have a keeper. its harder than it seems i dated a loooot before my boyfriend and i know for a fact that the little things just hanging out its hard because you have to also be friends , but once you get there its awesome.

  • sylvia

    My best date ever was with my current boyfriend. We went to an amusement park for halloween. There were special shows to scare people and they had haunted houses. It was som much fun and we lauched the whole day because they scared me too 😉 and after that we went to the fair at that same park, sitting on a bench eating curros. I think i enjoy the most the moments that you can be yourself and lauch at eachother.

  • Sam

    I completely agree. My best dates have been cozy night in playing games with my boyfriend or just cooking dinner together, or a simple date of drinks of a sweet bite to share over long joke-filled talks.
    I think it’s a sign of true compatibility to be able to have the best nights of your life with no plans whatsoever. If he really loves you – you’re enough, and vice versa.
    If every date needs to be bungey jumping to have a good time, good luck with that guy!

  • Ellie Monroe

    My best date was the first date with my fiancee! We only knew each other for about a month (possibly not even that) and we went to a house party for New Years. We were both nervous, but it ended up being the being of our wonderful relationship. Almost 2 years on New Years!

  • Ashley

    I have to agree that it’s the little things that matter. It’s important that you have fun sitting and talking, or playing cards, as a way to maintain a healthy relationship. But traveling is just as fun too 😀

  • McKenna W.

    I love simple dates over the extravagant ones. My first date with my husband was him taking me out on his land riding his family’s 4-wheeler, because I had never done that before (very city mouse met the country mouse!) It was all sorts of exciting because he showed me something new :)

  • Namrata from Namysstylenest

    You said it so well. I absolutely agree. You just have enjoy & be happy.

  • TheMrsG

    I totally agree! The best date I ever went on was my first date with my now husband. First off, I loved that he made sure I knew when he asked me out that it was a date. I hated when I was single, and a guy would ask me out, and I would wonder if it was a date or just a “friends” dinner… My hubby made sure I knew his intentions! Secondly, he was such a gentleman! I’m an old fashioned girl, and love that he brought me flowers, opened all the doors for me, drove, and paid. We went to dinner, and closed down the restaurant just sitting and talking! We didn’t want the night to end, so we went out two stepping. We danced, laughed, and talked all night long. It was such a simple, typical date, but our connection made it much more :) we are now married; celebrated our 1 year anniversary in November. We still love going out dancing together.

  • cuckl




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