Goals Series Continued: Date Nights!
Basically, I want more of these.

One enormous positive development is that A will be 13 soon and I have decreed that to be a reasonable threshold for babysitting, particular if we aren’t going very far (discussed previously in this post – lots of helpful comments!). (C is almost 11, and G is 7 – so it’s not like there are a gaggle of toddlers to contain either, though sometimes you might think so based on the noise level of our home).
I love family time, but I also love hanging-out-with-Josh-sans-kids time. Sometimes we need to have a conversation about adult things, or just an interrupted string of thoughts.
I actually think we were better about regular date nights when the kids were really little and we just needed the break, and have had less of them in our current era. Maybe it’s in part because getting a babysitter has been less magical in recent times — when we get home 90% of the time at least one tween is still up, too. This is fine (and appropriate!) but I still want it to be just us sometimes.
So, my goal is at least one per month, and ideally more. We are already behind; I don’t think we had any in January yet, and he is on call this coming weekend. We will have to make up for lost time in a future month!
Some of these can be double dates (funny side note: Josh says this does not count as a date? I think it does, but I get that it’s not the same as 1:1). But most will be 1:1. One barrier lately has been that his call schedule has not been provided with a lot of warning and that makes it hard to plan (even if you loooove to plan, there are challenges!). Still, I think we’re about to get Feb + March and I am going to slot in some date nights or (?) days. Maybe even 3!
I’m also hoping/aiming for two couples trips this year – one in May (Bayshore marathon) and one (?) in the fall or winter, or possibly while the kids are at M-F camp (ALL 3 are going for 3 weeks) — though we will get 1:1 time even if we’re just at home during that time which will also be nice.
As an adjunct to this goal, I want some better DATE NIGHT OUTFITS. Because feeling like you look cute on your date adds to the drama/fun, doesn’t it!? I have a few tops, not enough bottoms (really we’re reaching crisis level here), and I also feel like I need a new pair of shoes.
Any date night wardrobe recs!?
Am I overthinking it (probably)?
Any fun date night IDEAS? (one indulgent idea I have is to get a couples massage first, then go for drinks or dinner after, but it has yet to actually come to fruition.)

22 Comments
Stichfix! I’ve gotten some awesome jeans, sweaters and tops!
Agree. The quality isn’t perfect but for the cost and effort level on something you won’t wear all the time, it is hard to beat.
My suggestion will be a little different: secondhand/consignment/thrift stores…. especially if you are looking for “date tops.” There’s typically a lot more variety of options than you’ll find in any given store and I’ve found a couple of things that fit the “fun top” category really well. I appreciate the wide variety, particularly if the store is well organized. I go to one that is organized by category, then size, and then color within the size and it makes my heart sing.
For date nights – is there sailing, mini golf, ceramics lesson, cooking lesson? You are both interested in kinetic movement – might be very fun!
I like going out to dinner and going to walks with my husband. Occasionally we go and have a beer at a local place. Neither of us would be into massage or art based dates. I don’t like concerts either. We need more ideas too that don’t just involve drinking or eating too much food.
I like the mini golf idea Kate mentioned but I don’t think the weather where you are would be ideal for that right now …
Bowling? Trying to think of indoor stuff …
My summer date night outfit is a white dress and sandals. My winder date night outfit is dark jeans and a black silk blouse. I have a couple of each of the above and rotate them a bit. Spring and fall we tend to do after work dates in NYC (one of my goals this year is to do a monthly date in the city) and then I snaz up my work clothes but I know weekday dates don’t work well for you.
Your outfits sounds so good!!
Equipment has really nice silk blouses that work well for this sort of thing. I have one I got on sale 8-9 years ago which is my go-to for this sort of thing.
I’m always on the hunt for new date ideas, since if we don’t watch it we end up in a rut of having dinner and then hitting the couch. Last year we started biking a 100 mile bike trail in out and back segments, and I’m looking forward to picking that up again in the spring. I also want to visit some wineries and breweries.
I’m a big fan of double dates, and hey if they don’t count toward the goal that’s fine because they can be a separate goal!
How about either some fresh jeans or pants in a cropped, wide leg style for date night? Check out Quince for super reasonable prices and good quality. How about J. Crew or Madewell for easy tops? Check out Sorrel and Sofft brands for great wedge sandals and shoes.
Bonus Quince is a BOBW sponsor! Okay great suggestions (as always)
My goal is quarterly date nights!! We had our first on 1/11. It was a group date to a really fun indoor mini golf course bar type of place called the puttery. I counted it as a date. It’s diff than 1:1 but we had time to chat on the drive to and from. We go to Mexico for 4 nights in March so that will be amazing!! We are going with 2 other couples but will get plenty of alone time I’m sure!! I love the idea of a day date but we would need to take time off and that is harder to do.
My goal is monthly date nights! We got January and February is already on the books, so good progress so far. I would count a double date as a date night but my husband is probably more on Team Josh there!
Cold weather date night outfit (like Nov-Feb here in NC) is dark jeans or faux leather pants (I have a pair I love from J.Crew!) and a fun blouse. Warm weather is a dress, always! I love looking for my fave brands on Poshmark and TheRealReal to get secondhand but good condition date night outfits (especially “going out tops”).
My warm weather date night outfits are a dress and sandals. Cold weather date night outfits are usually jeans, boots or loafers, a silk blouse and a blazer. I add more jewelry and bring a smaller bag to make it feel more date night-ish. I have a pretty small wardrobe, but that formula works for all but our fanciest nights out and I feel like myself. I’ve found some good tops and shoes on TheRealReal to mix things up.
In Europe, we swear by Zara for many, many date nights because they make $30 copies of high end fashion. They sell in US and have sales now. Do you have Cirque du Soleil coming to town? That is always fun. But frankly going to a great winery never gets old.
I’m the wrong person to ask because a)my wardrobe is currently a disaster and b)my husband and I rarely have date nights! His birthday is next week though, and he’s requesting dinner and a movie. I haven’t been to a movie in a couple years.
I solved the planning of dates by gifting my husband 12 dates (1 each month) every year for Christmas! This is year 3 and we’re going strong. Usually we end up with a few extra in there, and we’re trying this year to make time on Saturday nights to hangout with a tv show or game if we’re both home. Some of our favorites: mini golf, cooking class (usually small group), Blackhawks games (we have partial season tickets, this is kind of cheating), an outdoor concert & picnic, high ropes course/rock wall climbing, brunch after we play a soccer game together, annual holiday date with friends (do all the Christmas stuff in downtown Chicago), fancy cocktails or a distillery/brewery visit, trail biking. We’ve also done trips the last couple of years, and this year we’re trying a comedy show and restaurant week for the first time in awhile!
that sounds awesome! I totally would do a comedy show. and trail biking also sounds really fun!
I keep an eye out for special night events at museums etc – one near us has adults only evenings, or opening night for art museum exhibitions, concert nights at the botanical garden etc. It feels special and is something different.
My husband and I both have Wednesday morning off with childcare built in during the school year and we treat that as our “date time”. It’s a game changer for us because 1) I have an autoimmune disease I’m in treatment for and my energy levels are often quite low in the evening, it’s hard to go out and be fun. 2) we sometimes go out to brunch/lunch but we usually stay in, chat and connect. It’s a great solution for this phase of life with my health issues/having 2 young kids. Summer is much harder for us! We also are season ticket holders to the symphony and that helps because we pay for it ahead of time and it’s already on the calendar a year in advance.
That sounds so so nice!