Living in Sin: The Thing About Double Dating (+ a $100 giveaway!)

by Rachel on December 18, 2011

One of the new experiences I’ve had since I’ve started dating Eric is the double date. I always thought of double dates as something that only happens in episodes of “Happy Days” and not a real thing that actual couples do. But not long into our relationship, one of Eric’s friends actually suggested that we “double” with him and his girlfriend.

I, of course, was totally thrilled. I mean, yes, I thought double dates were an only-on-TV type thing, like huge dorm rooms painted bright colors, but that doesn’t mean I don’t want those things. So I’ve been totally cool with double dating. Every time Eric and I get invited on a double date, I start making plans to put on my best poodle skirt and imagine that we’ll be splitting strawberry shakes with our dates and then going to Makeout Point.

(Makeout Point also seems like an only-on-TV type thing that I really wish were a real thing. When I was in high school, I actually tried to make it a real thing. It wasn’t quite as cool as Hollywood makes it seem, although the same goal was achieved.)

In the 18 months since I’ve had a boyfriend, I’ve learned a few things about double dating. First, that milkshakes are rarely involved and second, that it’s way harder to plan a double date than one might think.

Problem #1. The other couple.

The first thing you need for a good double date are good couple friends. Now, I always assumed that couple friends just naturally happen when you’re part of a couple, but this is only semi-true. Yes, you can find other couples to go out with, but that doesn’t mean you are going to want them as couple friends. First, everyone has to get along, and the fact is, probably only two of the people are already friends.

What I’ve experienced/heard from my girlfriends is that if the men are the ones who are already friends, they just assume the women will be fine and will completely hit it off (because all women just bond over talking about babies, you know?) and can just entertain themselves from there. Guys don’t understand that you might not dislike the other woman, but that also doesn’t mean that you want to plan a group vacation in which they can just go out golfing because the women are going to be fine to go get mani-pedis and go shopping.

Every time Eric and I hang out with another couple, I know that the two already-friends are holding their breath, desperately hoping the two not-yet-friends will totally bond so we can be like, “OK! We found them! We found our couple friends! We’re done looking!!!”

But then there’s always the secret fear that when you do find the perfect couple friends, they are going to turn out to like you a little too much, and you’ll soon find out they are swingers.

Problem #2. Making Plans. 

Making plans shouldn’t be a problem if you’ve found the perfect couple friends, but if you’re not there yet — if you’re still testing the waters and courting each other (which is very much like dating and that totally sucks because at this point, you thought those games were over) — you have to try to find something that the other people will think is cool/affordable/a good idea. Every time I get a cool Groupon or Living Social deal, I’m thinking, “Is this something that would make a good double date? Do they seem like rocking climbing people? Would they like to go make our own fudge and then hit this BYOB pottery class? It’s only $6 per person…” With so many daily deal sites, it feels lame to just go out to dinner, but then I think, What the hell is wrong with a delicious dinner?!

Once an activity has been selected, it’s even more complicated to actually make the plans. Every couple I know has a really complicated schedule that is very hard to get into. I’ve found that the best way to schedule a double date is plan it at least a month in advance and to not aim for hanging out every weekend. That’s another thing about couple friends on TV: they hang out all the time. In reality, no one has time for that. (Unless two of the friends are actually related because then double dating is actually just “family time.” Oh and just FYI, if you are trying to make couple friends with a couple who already has couple friends and they are related in some way, like the guys are brothers…good luck with that. You’ll never break into that circle unless you’ve been friends since high school and even then, it’s still just a maybe.)

The Double Date

Last night, Eric and I did go on a double date that was, miraculously, planned in just a few days. Last week, I volunteered to try out a new app called Serve that comes from American Express. Basically, it’s a sexy way to split the bill when on said double date. (Dealing with that is definitely Problem #3, but it’s a problem in any group meal setting, not just double dating.) Serve said they’d treat people to dinner if they went out and tried the app, and, because I’m the kind of girl who will do about just anything for a free dinner (it’s how I ended up with a serious boyfriend in the first place), I was really hoping I’d get to try it out.

I was excited to find out I’d been chosen to try it but then I realized I had less than a week to plan the double date, and, given the issues I outlined above, I was kind of worried it wasn’t going to happen. Luckily, Eric and I have a couple who we’re friends with (I really like them but I don’t know if I should call them our Official Couple Friends because that’s a big step and we haven’t really talked about it with them yet…although I’m not sure if you talk about making that official like you do a typical relationship) and they were able to go out to dinner last night so we could try out the app. Kyle and Mindy are always busy or out of town, so it’s hard to find time to hang out with them. The good news is that once we do, it’s easy to make plans because they are total foodies. Every time we hang out, Eric and I basically say, “Tell us where we should go out to dinner and we’ll see ya there.” For last night’s outing, they suggested Lucio’s in Houston, a BYOB (I LOVE BYOB RESTAURANTS!) that serves all sorts of delicious food. (And they serve it in very dim lighting, unfortunately, so I have no pictures of the fabulous meal I’m about to describe.)

I have to say that as far as double dates go, this was one of my favorites. First, the food was amazing. The waiter opened the first bottle of red wine that Kyle and Mindy had brought as we looked over the menu. First, we chose appetizers. I had read a review of Lucios’ online that basically said, “You’d never think to order spinach dip at a restaurant like this, but you should,” and we decided to take that advice. I’m glad we did; it was the best spinach dip I’ve ever had — warm, super creamy, with homemade fried pitas that tasted like they had a little funnel cake batter mixed into them. I also ordered the French onion soup for another starter; I love French onion soup and this was the best I can ever remember having (the beef and pork broth didn’t hurt, plus it was topped with a big puff pastry).

We had a pretty hard time choosing main courses because it all sounded so good, but eventually Eric ordered the New York strip steak, I ordered the filet mignon with asparagus and some of the most delicious mashed potatoes I’ve ever had (I know I keep saying that but it was one of those meals), Mindy ordered the salmon, and Kyle ordered the scallops with butternut squash risotto.

The food was good, but the company was great. I felt like we never ran out of things to talk about and we were laughing the entire time.

You Got Served

When it came time to pay the bill, I whipped out my phone to try the Serve app. Now, the idea behind this app isn’t totally new — the service itself is similar to other money transferring services — but I think they are taking a smart angle by pitching it as a way for friends to split the check at dinner. Unlike other similar apps, this one comes with some fun tools built in, like the “Split the Bill” tool (enter the total amount of your bill, calculate the tip, use the sliders to show exactly how much each person owes what, and then send them a money request right from the app) and the “Pizza Party” tool (enter how much the pizza cost, how many slices there were, and then ask your friends how many slices they each ate — therefore making the person who ate the most pay more without singling them out — and then send them a money request right there).

When you set up an account, Serve also sends you a debit card with the AmEx logo on it; it’s linked to your Serve account and you can use it like a pre-paid debit card at ATMs or just to just like a regular debit/credit card all over town, avoiding the whole “OK, I just paid for this out of pocket, so now I have to wait for my friends have to send me the money and then I have to transfer the money back to my bank account, and god I hope it comes through before my rent is due” thing that some of us have experienced with other apps.

I really like the app (honestly, the “Pizza Party” tool just makes me laugh every time I think about charging people per slice); I’ll definitely continue to use it and encourage my friends to sign up (because obviously it’s the kind of thing that works better if your friends are already using it too). To get more people to start using it, Serve is offering a giveaway — you can win $100 in your Serve account! (The $100 can be used on a nice dinner or you can just blow it on a trip to Target; it’s totally up to you.) To enter to win, just leave a comment on this post by December 25, 2011 at 11:59 PM PST and you’ll be entered to win!

Things I’m legally required to say: As part of the Foodbuzz Tastemaker Program, I received a $250 stipend to try Serve from American Express. Sign up for Serve and receive $10 credit towards your first use. Comment below within the next 7 days for your chance to win an extra $100 credit to your account! Official sweepstakes rules and regulations may be found here:

Over and out!

{ 69 comments… read them below or add one }

1 Courtney December 18, 2011 at 11:48 am

I’ve seen this serve thing on a lot of blogs and am interested in trying it out for sure!


2 Keri December 18, 2011 at 11:49 am

This sounds like a great idea – it would have made things much easier when we’d go out in big groups in college!


3 Lauren December 18, 2011 at 11:54 am

very good – I’m definitely going to download it!


4 Summer December 18, 2011 at 12:02 pm

Sounds like a neat idea! Figuring out who pays for what is always my least favorite part of going out to eat with a group.


5 Melissa December 18, 2011 at 12:12 pm

I just found this app on my Android phone and downloaded it. Im so excited to use it for the first time. This app is going to make things a whole lot easier. Im so tired of looking for separate apps, when this has cut time down into one.


6 Jaclyn December 18, 2011 at 12:27 pm

Well, I’m food-motivated, so this sounds good to me!


7 Lauren December 18, 2011 at 12:42 pm

This sounds like it has a lot of potential. There are so many great restaurants in our area that won’t split the bill, and that always turns awkward!!


8 Brittney December 18, 2011 at 12:49 pm

Serve sounds like a cool idea! I agree, it’s tough to make the double date work out perfectly but it can definitely be fun and mixes things up!


9 Sara December 18, 2011 at 12:52 pm

I go out with my friends so much and we always ask for separate bills…I’m sure our waitresses hate us! This sounds cool and I’d love to try it.


10 Erin December 18, 2011 at 1:01 pm

The pizza one makes me laugh — I can’t imagine quibbeling with my friends over who had two pieces of pizza and who had three — but it sounds like a cool app for those awkward end-of-dinner moments when you’re trying to figure out who owes what without making your poor grad school friends pay $40 for a side salad.


11 Sable@SquatLikeALady December 18, 2011 at 1:15 pm

This is the first time I’ve heard of this! Wow! Awesome tool. I could definitely get a lot of use out of it — our couple-friend is my husband’s cousin & his girlfriend, soon to be fiance, and they just moved in about 50 feet from us haha!


12 Alli December 18, 2011 at 1:16 pm

Ugh I feel you on how hard it is to find couple friends – so far the only one where we get along with both lives 4 hours away. Everybody else has been mostly a miss.


13 Samantha M. December 18, 2011 at 2:15 pm

Yay for couple friends! This year we finally found our local couple friends, and it’s even a three-way (Hey-o!). We’re even hanging out with them the 23rd to have a “friends-mas” before we get caught up in the craziness of the holidays and don’t see each other until the new year. =D

Also, that dinner sound incredible and I’m officially jealous. I’m also jealous that you have a place where you can BYOB, that doesn’t seem to exist in Northern California. =/ Happy Holidays!


14 Michelle December 18, 2011 at 2:17 pm

Sounds like a great app. I’m excited to try it!


15 megan December 18, 2011 at 2:26 pm

This sounds like a useful app. Downloading now!


16 April December 18, 2011 at 3:05 pm

Sounds pretty interesting. We don’t eat out super often right now, but it seems like an interesting app.


17 Heather December 18, 2011 at 3:05 pm

Ugh. Finding couple friends makes me want to slit my wrists (in a totally non suicidal way). I’m 23 and my husband is 27, and as you can probably imagine, ALL of our friends are still single or in very new relationships.


18 Kehinde December 18, 2011 at 3:17 pm

I’ll pass on the pizza app, I am not charging my friends per slice! Haha.
Yay for finding time to spend with couple friends!


19 Lindsey December 18, 2011 at 3:37 pm

I keep seeing this on other blogs, it looks super cool.


20 Jordan December 18, 2011 at 3:53 pm

Ugh, finding couple friends is the WORST, mostly because it’s so difficult. After nearly two years together, my boyfriend and I are still searching.


21 Laura December 18, 2011 at 4:08 pm

Sounds like I good app if other friends are using it. I am going to look a little more into it, I’m not sure totally “get” all of it.


22 heather December 18, 2011 at 5:11 pm

i cant wait to try that app! seems like its a real headache saver.


23 Julia December 18, 2011 at 6:04 pm

I hate having to deal with splitting the bill, especially when it’s a big dinner party for someone’s birthday or special occasion! I’d definitely like to try this out :)


24 Manon December 18, 2011 at 7:07 pm

Totally trying this app!


25 Anne December 18, 2011 at 8:46 pm

Everythign you just said about double dates is completely true!! They can, however be a blast of you find that perfect match for both members of the couple :)


26 Liz @ iheartvegetables December 18, 2011 at 9:00 pm

That’s a cool app!!! And it’s SO True that its almost impossible to find couple friends. When my guys BFF started dating a girl I liked, it was awesome! And then they broke up.


27 Nicole @ Giraffelegs December 18, 2011 at 9:55 pm

double dating is way harder than normal dating. dying.


28 Jess-ThatJessGal December 18, 2011 at 9:56 pm

You are the third person this weekend to mention Serve. I sure could have used it 2 weekend ago when an awesome celebratory lunch turned into a huge CF when the server wasn’t allowed to split the bill for us and not everyone was carrying cash.


29 Rachel December 18, 2011 at 10:11 pm

Ahhhhhh I’d LOVE a $100 dinner out… just what I’d need after the crazy holidays : ) That app seems great… the pizza party tool is hilarious… I’d love to see it in action HA!

And, love your advice and points about double dates… I’ve definitely had my awkward ones. You are so right how guys always think all the girls at the table will be BFF. So NOT the case…


30 Aleksa December 18, 2011 at 10:54 pm

I would definitely use the money for a target trip!


31 JordanBailor December 19, 2011 at 1:04 am

Nice! I haven’t really tried double dating yet… I mean, we go to dinner with other couples before date parties and stuff, but I feel like that doesn’t really count. Especially since you’re just eating so you can go get drunk right after (as that is how you properly do a date party). As for what I would spend the money on… Target. Target Target Target. Poor college girl needs some new stuff!


32 Erika December 19, 2011 at 4:29 am

BYOB restaurant?! Seriously? Man, why don’t we have those in Washington?


33 Jamie J. December 19, 2011 at 9:00 am

Seems like a really useful service. I’m all for skipping the awkward how-much-do-we-owe-how-do-we-split-it moment.


34 Katie December 19, 2011 at 9:46 am

Hey Rachel–It is fun to see restaurants that I’ve also loved on your blog! That spinach dip seriously is amazing. I always wonder if they would totally look down on me if I went there and just ordered two spinach dips. The fried pitas slices make it…and BYOB doesn’t hurt.


35 Kavi December 19, 2011 at 9:50 am

What a great idea! The pizza party app may have come in handy back when we were all broke college students ;) Glad that you found some new couple friends to hang out with!


36 [SMASH] December 19, 2011 at 9:52 am

Wow, that sounded like an amazing dinner! We do the couple dinners every once in awhile but honestly, I’d rather it just be myself and my boyfriend. Couple dinners are too much work… Unless it’s with my bestie and her husband!

I hope I win this $100 credit for Serve! :)


37 Joy December 19, 2011 at 10:06 am

What a great dinner! And a fun giveaway


38 shelby December 19, 2011 at 10:17 am

Oh couple-friend-dating. It’s so much more complicated than it should be! Glad you had a nice night out with friends.

The serve things sounds interesting, although it seems like a pretty big hurdle is that everyone in your group would have to have a smartphone and an account, right?


39 Jacki December 19, 2011 at 10:42 am

Ah yes, friend dating. It IS more complicated than it seems. We don’t have many couple friends around here but I’m working on that.

I will definitely be checking out this app! I read this post last night on the way home from Christmas shopping with Matt and it inspired him to say we need to go out for a nice dinner soon. So yay! Hehe.


40 Mal December 19, 2011 at 11:04 am

This is a great idea! And I just finally joined the 21st century and got a “smart phone” so I can actually use it now!


41 Lizilla December 19, 2011 at 11:18 am

I’m glad you had a good double date. Every time we go out on a double date the other couple gets in an argument, is super rude to each other, or the girl usually says something way to personal about the guy. Definitely has lead to my husband and I consuming several bottles of wine to drown out the awkwardness.


42 ashleigh December 19, 2011 at 11:47 am

Sweet giveaway! I always hate when the check comes because my meal is always the cheapest and I always end up paying so much extra.


43 Stephanie December 19, 2011 at 12:33 pm

I think I’ve been pretty lucky so far in my hunt for couple friends, but I feel you on the difficulties that go along with it. It seems like you are well on your way with these two though, and at the very least you got a great meal and a chance to try a fun new app. I’d love to try the app myself!


44 Lynda Del December 19, 2011 at 1:03 pm

This sounds like a great app to use! Thanks for the chance!


45 Ashley December 19, 2011 at 3:22 pm

I definitely feel you on the couples friends front. My fiance and I have ‘couple friends’ but if we get together once a month, it’s considered a success. Looking forward to trying the app!


46 Mel December 19, 2011 at 4:03 pm

Oh gosh, this app could definitely come in handy with some check-splitting disasters I’ve had! I love this post though because my one real couple’s night out experience was during one of my first date-cations in DC: me, date, 2 of my guys’ couple friends, pizza, saki bombs… and my constant phone calls from my friend trying to meet up, who happened to have no idea what was going on because she was on ‘shrooms. Needless-to-say, the night sorta ended in a dramatic fight in the bar/ streets/cab/ apt. (Sorta like the crazy, pink-haired lady fiasco..) At least the other couples were nice!


47 Isabel December 19, 2011 at 8:10 pm

That’s a useful application to have! It’s always horribly embarrassing when you go out to eat with friends, realize that half of you are science/math/engineering majors…and none of you can figure out how to split 35$ into six. And then who owes who for what, do they make it up by paying for the next dinner…really it shouldn’t be that complicated, but oh yes it is! (Then again, maybe that’s a teenager thing. One hopes it becomes easier with time)


48 Lindsey December 19, 2011 at 10:43 pm

This app sounds like a legit good idea. I hate when everyone gets flustered and someone inevitably says “let’s just split it 4 ways.” Um, no. Not when you had the 32 oz ribeye and I had a Cesear salad.


49 Kat December 19, 2011 at 11:14 pm

This sounds like an app I would totally use. Except its ridiculous to ask someone how many pizza slices they ate tho … :) why is paying for a meal with your friends so awkward and weird? Oh that’s right – because all my friends are cheapskates who try to get away with paying less than they owe and conveniently forget about tax and tip. Yup, I need this app!


50 Arlene @ Adventures in Weight Loss December 19, 2011 at 11:50 pm

I just read about the Serve app somewhere else … the company must be making a marketing push. Sounds interesting, even if I don’t go out to eat with large groups very often.

If I won $100, I’d make it a point to find a group to go out with! ;)


51 Phoebe December 20, 2011 at 2:18 am

I love doing math in my head so I have never really felt the need for this kind of app . . . I would totally like to enter to win though. ;)


52 Laural December 20, 2011 at 9:17 am

The pizza slice feature is funny. Reminds me of when I would get pissed paying for ONE slice of pizza at Pizza Papalis when everyone else ate their weight PLUS pitchers of beer (before I was of age). I would get so. angry. After all was said & done, it would be a $20 slice! Ha!


53 Gee December 20, 2011 at 10:30 am

I’ve signed up with serve!


54 Aubreylaine December 20, 2011 at 1:07 pm

I would love to win!
littlegray88 at yahoo dot com


55 betsy December 20, 2011 at 1:08 pm

Great idea, I love all food-related aps! I would love to be chosen on 12/25 – my birthday!


56 Shannon December 20, 2011 at 10:19 pm

The title of this post certainly got my attention!


57 Elizabeth December 21, 2011 at 9:24 am

I signed up for a Serve account. Sounds cool!


58 Julie Lynn December 21, 2011 at 9:38 am

The pizza party portion of the app made me laugh out loud!! Can’t say I wouldn’t mind a free dinner, *coughtriptotargetcough*, for my upcoming anniversary!


59 lynn @ the actor's diet December 21, 2011 at 11:15 am

i signed up for serve too – and would love an extra $100 in my account!


60 zoey December 21, 2011 at 2:51 pm

Would love to win 100 for a night out!


61 Erin @ Girl Gone Veggie December 21, 2011 at 6:48 pm

I signed up for a Serve account!


62 Christine December 22, 2011 at 12:01 am

I signed up with Serve.


63 Erica Best December 22, 2011 at 12:49 am

I signed up for a Serve account!

purple_lover_04 at msn dot com


64 Helen December 22, 2011 at 11:28 am

I just signed up for Serve the other day and I’m still trying to figure it out.


65 Kimberly December 22, 2011 at 6:38 pm

What a great blog!!

Serve is a great idea! I signed up through FB & my email address ~

Have a great Christmas & New Years! :-)


66 Whitney December 23, 2011 at 4:19 pm

Sounds like a great concept, I’d be interested to try it out and see how well it actually works!


67 anna pry December 23, 2011 at 11:33 pm

i have a serve account


68 Bria @ WestofPersia December 25, 2011 at 6:51 pm

Hmmm, interesting app, and you bring up excellent points about double dating.


69 Traci December 27, 2011 at 6:38 pm

Love Serve! What a great service! Signed up at


Leave a Comment

Previous post:

Next post: