Teenagerdom for the middle-aged
April 24, 2018 8:41 PM   Subscribe

What are some cute "first relationship" style experiences I can give to my late-bloomer boyfriend?

I am a late-30s lady in a newish relationship with a mid-40s man. It's going well, we are sickeningly happy and in love and all that good stuff.

We have talked about past relationships a bit, and to my surprise (he is an awesome guy and very emotionally switched on) it turns out that he is extremely inexperienced and has spent much of his life single and feeling very lonely. He feels like he has missed out on a lot of things over the years. So, naturally, I want to do all the nice things for him and show him how much I appreciate him.

However, I am not the world's most sensitive person, and I am also not used to being the more experienced party. My previous relationships were all with quite cynical people who didn't place much importance on making each other feel good, or on your typical relationship milestones. So I don't really have much personal experience to go on here, hence picking the brains of strangers from the internet.

So the (hopefully not-too-chatfiltery) question is:
Can people suggest some "first relationship" experiences/activities that they found meaningful at the time?
If you are an older inexperienced person, what things do you feel like you missed out on, that you would love a partner to provide?

Generally I would just ask him what he wants, but surprises are nice too :)

Thanks everyone for your ideas.
posted by procrastinator_general to Human Relations (29 answers total) 15 users marked this as a favorite
 
Have you and he specifically talked about whether he wants at this point to experience some of the things that he feels he missed out on? It's possible to simultaneously regret not having had some experience and also not want to have that experience now. E.g., I'm a little sad that high school me was out of town the night of his prom, but I suspect that current me would find a high school prom distinctly under-whelming.
posted by d. z. wang at 8:54 PM on April 24, 2018 [4 favorites]


Go to six flags! 'Play hooky' and go to the beach (or whatever is nearby). Make out in your car (drive in movies?!)! Buy cheap wine and write terrible poetry together. Have a night picnic and sit under the stars!

So much good stuff. I am going to brainstorm and come back in a bit. I love this question.
posted by Literaryhero at 9:00 PM on April 24, 2018 [4 favorites]


Ride your bikes nowhere in particular at night.
posted by michaelh at 9:01 PM on April 24, 2018 [8 favorites]


Leave a cute note folded up in his coat pocket.
posted by mochapickle at 9:02 PM on April 24, 2018 [8 favorites]


Walking at dusk in June.
posted by JamesBay at 9:09 PM on April 24, 2018 [2 favorites]


Most of my really formative teenage relationship moments came from the fact that we couldn't hang out at home really. Drive-in movies, parking at the duck pond, sitting outside the IHOP (late at night, overcaffeinated) talking on the benches, going for walks, driving around, mostly-pointless mini road-trips.
posted by Lyn Never at 9:19 PM on April 24, 2018 [11 favorites]


This is so sweet and heart-warming, how kind of you and fun for you both! One of the best things about being an adult doing teenage stuff is all the fun without any of the awkwardness. Oh, and you can legally drink alcohol and don't have to report back to Mom and Dad! I'm a high school teacher so I feel this every day.

I second the recommendation to recreate a prom. It could just be dressing up and taking cheesy photos together, listening to a mix tape with favorite hits from the time, then going out to eat at fancy restaurant. If you use social media, please post photos to share with friends because they'll be happy for you.

Speaking of photos, take a ton of selfies together when you're out and about -- both for exciting trips and the like but also mundane stuff like sitting on the couch together. You could get Snapchat and send each other silly videos. This is more contemporary but still fun!
posted by smorgasbord at 9:22 PM on April 24, 2018 [1 favorite]


Just interjecting to say maybe bias towards the easier/simpler suggestions, as some of the fancier ones proposed here would ... not go well ... with me, were I in his shoes, and I’ve lived my life in some very similar shoes.

There’s a difference between trying to make up for lost time, and rubbing someone’s nose in their wasted years.
posted by aramaic at 9:50 PM on April 24, 2018 [9 favorites]


I am a 50 something divorced male dating a 50 something female who has never been married. She has had an extensive dating life, but never married and never lived with anyone. She asked me one day what we could do to simulate what it is like to be married. I told her we should sit on the couch with our own laptops, mindless tv on in the background and not speak to each other for three hours, then argue about who was supposed to go grocery shopping and didn't.

While I like the idea, love the sentiment, I am not sure you can make up for lost time by forcing the issue. I think it has to happen organically and some experiences a younger couple might have are simply lost to time and are not going to have the same resonance as it would if it happened 15 years ago.

I think the best thing would be to park on a lover's lane and make out.
posted by AugustWest at 9:56 PM on April 24, 2018 [14 favorites]


Write him a love letter. Leave a mushy, affectionate voicemail message. Give him a book that holds some significance and include an inscription. Create a music playlist. If it's feasible, arrange to pick him up from his job and go out to lunch or dinner. (One early-relationship milestone that's weighty is "public recognition of coupledom.")

Take a weekend trip. Stay at some B&B, or a small hotel, within 2-3 hours of your city. Go antiquing, see some historic attractions, visit the museum or aquarium, go hiking. Hold hands a lot. Take pictures. Pack a nice outfit for your dinner at the reservations-needed local restaurant. Buy souvenirs, even if it's only a fridge magnet, to remind you of the trip.

Go to a concert, have a great time, and wind up at a 24-hour diner. Stay out until early morning, and talk so much you're hoarse the next day.

Make a point of seeing the sunrise or the sunset while on a beach or near a lake.

[Faux-prom would give me hives, so I'm thinking more along the lines of relationship milestones from my 20s.]
posted by Iris Gambol at 9:56 PM on April 24, 2018


Make mixtapes for each other. (Or mix-playlists, or mix-CDs. Probably best to skip the "tape" part.) Feel free to use whatever music you find meaningful, not whatever's on the charts today.

Play games together - either ordinary board or card games, or the romantic/sensual versions. (Naked Twister. Truth or Dare. Sexy couple boardgames. Two player tabletop games. 2-player RPGs.)

Go on a fancy date - full formal clothes or your most exotic costuming. Pick a restaurant you both love, and feed each other parts of your meals. If you wind up wearing renfaire clothes to your favorite burger joint, fine - the point is to dress up so you feel attractive and your partner's eyes are only on you, and that you're in a place where you're comfortable having fun together.

Buy little gifts for each other: keychains, tourist mementos with a favorite animal on them, funny socks or novelty hats.

Pick a date that's meaningful for anniversaries - first date, first kiss, first meeting, whatever. Celebrate it often: six week anniversary of our first kiss; three month anniversary of the first time we stayed up until 3 am talking.

(Stay up until 3 am talking. Since you're adults, this is allowed to involve booze and/or coffee.)

Go shopping somewhere you both enjoy, and hold hands as much as possible.
posted by ErisLordFreedom at 10:05 PM on April 24, 2018 [3 favorites]


Here are a few things I wished that a special someone would do with me in high school:

Go to a movie in a theater and hold hands.

Split a drink at a soda fountain. Bonus if it's an ice-cream soda (do those even exist anymore?) and you use two straws.

Attend each other's sporting events (workout sessions might do in a pinch?) and cheer.

Have a romantic picnic in a park.

Go for a bike ride together.

Go to a concert - bonus points if it's a band you loved in high school - and buy each other swag to wear.

Send each other carnations on Valentine's Day.

(Needless to say, I was a teenaged romance junkie when I was a teen, and a lot of what I longed for was firmly in the past. It was still fun to dream about, though).
posted by dancing_angel at 10:25 PM on April 24, 2018 [1 favorite]


Lie on the hood of the car and talk at night
Make out in public places
Go for walks with an alcoholic drink in a thermos
Play the music you liked in high school / college while you fool around
posted by pseudostrabismus at 10:31 PM on April 24, 2018


Staying up all night kissing & talking, into the early hours of morning.

This is something my partner & I still like to do, when we have a chance! There's something wonderfully intimate about talking for hours in darkness; reality disappears and it's like you're in your own little world, just the two of you.
posted by fire, water, earth, air at 11:59 PM on April 24, 2018 [2 favorites]


Go hillwalking at night to see shooting stars.

We still go out and get icecream and walk somewhere.

Drinking videogames (ok it was drinking Mario party played as a group but my sweetie was there). Strip poker.
posted by stillnocturnal at 12:33 AM on April 25, 2018


Some of my most formative dating experiences were exactly what Lyn Never says: pointless road trips to, like, a slightly further away grocery store than was really necessary. Wandering around the gardening department and shyly flirting, feeling out each other's music tastes by flicking through the CDs, buying a boxed cake mix to make later.

We did these things because it was the only way to be alone, really - an excuse to be away from our friendship groups and our families, with just enough cover that neither of us would have felt exposed or vulnerable if it became clear it wasn't really a date. That sort of sweet, awkward, nervous anticipation when you're not really in control of most of your life and have little freedom but you're excited about the future.

I don't know if it is even possible to recreate that, as an adult with agency and confidence - but that would be the experience I missed most from my younger dating life.
posted by citands at 2:56 AM on April 25, 2018 [1 favorite]


This is a sweet sentiment, but some things to think about:

I’d concentrate on making nice experiences for him, not trying to make up for what he missed. That might make him feel self-conscious about his deficiencies, and that you’re keeping track of them.

And also consider that he may not want his counterpart for all of these experiences to be with one person. If you’re going to be his last girlfriend, there’s no need to rush through these milestones.
posted by Borborygmus at 3:09 AM on April 25, 2018 [5 favorites]


If you're lucky enough to live near a big nice aquarium, teen and twenties aged me would like you to know that they are very excellent locations for: artistically lit couples selfies, shadowy nooks and crannies in which to kiss (but not get too handsy because there are lots of kids just around the corner), benches on which to publicly hold hands while gazing at fish, and adorable but overpriced gift shop plushies to gift one's special someone. Also, if you're really super duper lucky, otters.

A thing I know my brother found especially meaningful in his earliest relationships was a chance to think of really thoughtful (and frankly sort of odd) gifts for his partners. I also have a thing about giving gifts to people I care about but I'm more willy-nilly about it. It can be kind of weird to think about but sometimes being receptive to getting things can be a gift to another person, especially if you're older and sort of have all the stuff you need right now. Open yourself up to getting frivolous lovely or cute things, maybe start it off by giving him something small and fun in that "i saw this and thought of you" way, and see if he responds. This of course can vary wildly, lots of people have a bunch of hinky issues around gift giving and if it's obligatory or must be reciprocal and so-on, but if it's not something you already know about him it's worth a try.
posted by Mizu at 3:37 AM on April 25, 2018


I agree with the suggestions that re-create the sort of sentiments that your guy may be feeling like he missed, updated for who you both are today, rather that focusing on the specific details. Celebrating little, otherwise minor relationship anniversaries sounds like a good suggestion, as do the "acknowledge the relationship in public" sort of suggestions.

Metaphorically, if he's been emotionally under-nourished in the romantic relationship area for a while, then yeah, he's not going to feel comfortably "fed" right away even though the two of you have a great relationship - there's a sort of nutritional deficit there. But malnourishment isn't remedied by simulacra of food that an under-nourished person watched other people eat while they were hungry. It can be some of the same foods, but it has to be actual food with actual nutritional content. Likewise with your relationship - don't do relationship-type stuff that doesn't make sense for both you and your guy. Do do shmoopy teen romance stuff that you do both still like on its own merits. But focus on whatever it is that makes him feel loved, cherished, and secure in the relationship, that also comes naturally to you, and just do extra of that.
posted by eviemath at 4:42 AM on April 25, 2018 [2 favorites]


Response by poster: Thanks everyone for all your great ideas.

I didn't explain myself very well, but all the date ideas, little gestures, and so on, are exactly what I was looking for. I haven't done a lot of them myself, either, so it will be fun to make some memories together. We have the hand holding and making out in public sorted already, heh.

Thanks again, you are all awesome.
posted by procrastinator_general at 4:46 AM on April 25, 2018 [2 favorites]


It kind of sounds like the goal is less "make up for missed teenage experiences" and more "be a good partner to someone who likes sappy shows of affection more than you're used to" -- yeah?

Because there are some shows of affection that are pretty much timeless. Calling each other dumb shmoopy pet names is not an age-limited thing. Saying "I love you" is not an age-limited thing. Making excuses to travel together or even just run errands together is... kind of the opposite of age-limited, it's actually easier when you're an adult.
posted by nebulawindphone at 6:06 AM on April 25, 2018 [3 favorites]


A lot of my ideas were written stuff, it turns out:
-Hide little romantic notes in his pockets, luggage, house/apartment, etc.
-Write long, heartfelt cards/letters for special occasions or long trips.
-Write those "open when" letters.

Also:
-take him as a date to something important to you that he may not already be privvy to (family thing, work event, etc.) and share your excitement about introducing him to that aspect of your life.
-celebrate him and your relationship on social media, in whatever way is common/enjoyable for your particular community (cute instagram pic, noting a milestone, celebrating his achievement, whatever).
-take pictures of him, if he's the type to enjoy it (see here for an example of a sentiment like that).
-take note of some cute date (first kiss, first "I love you", first overnight, etc.) and plan a surprise somethingorother to commemorate an anniversary (can be as simple as bringing chocolate or whatever)
-do something a little extra caring when he's sick (chicken soup gift basket? help out by cleaning something that may be an extra-difficult chore?)
-handcraft something he'll enjoy (you may notice I'm a fan of gifts as a love language, I know this isn't true for everyone)
posted by mosst at 6:49 AM on April 25, 2018 [1 favorite]


another: pick a great TV show to watch together, and make a regular date out of watching it (or just demonstrate your commitment by refraining from watching it alone :P )
posted by mosst at 6:50 AM on April 25, 2018


Picnic in the park.
posted by salvia at 7:28 AM on April 25, 2018


Frantic making out in the back seat of the car. My BF missed out on that too, so we jokingly did the whole date night as teens thing (which as I'm almost 50 was hilarious). We then made out in the car. The added frisson when we got home & I joking said shhh You'll wake my Dad & we tried to have quiet sex was both exciting & hilarious. What ever you do do it with a sense of fun & laughter otherwise it's just a reminder of what he missed out on.
posted by wwax at 8:39 AM on April 25, 2018 [1 favorite]


There was an askmetafilter thread years ago about little gestures that people do with their beloved that had a lot of comments that might fit. I like sending my husband goofy postcards about how much I like him. Someone in that thread talked about Always acting like they were being reunited after a long time when they saw their person at the end of the day (ie, enthusiastic kisses, etc). Most of the best things I can think of are like that, a reiteration of how good and happy being with this person you love IS.
posted by ldthomps at 9:10 AM on April 25, 2018


Find park. Find wooded path. Make out.
"Pregame" then go out to a dance club.
Call him late at night and ask if he's doing anything and heavily imply you are game for a booty call.
Go on a date to a place like Dave and Busters or a bowling / arcade place, and get super competitive over silly games.
Hold hands and walk around the mall and people watch and joke to each other about the human animals we all are.
posted by WeekendJen at 12:18 PM on April 25, 2018


I love this question! So sweet. My experience has been somewhat similar to his and I'm a hopeless romantic, so here are my ideas (though I am also a lady):

Cards! This is the time to go and buy the schmoopiest cards from Hallmark and give them to him randomly.

Slow dancing! Late at night, in the kitchen or the bedroom. Not sure if I'd recommend music from his high school years though; better to choose something the two of you can make your own.

Sitting next to (rather than across from) each other in restaurant booths. Works particularly well in diners. You can cozy up, hold hands and lay your heads on each other. Also great for sharing food.

Celebrating Valentine's Day (in particular), birthdays, holidays etc. It feels really validating to have someone to share that stuff with. Someone to spoil who will also spoil me.

Other simple things that I like: being kissed/held in public. Walking into a restaurant and having reservations under his name. Having doors opened for me. Getting flowers, chocolate, typical cliche romantic stuff. Also, buying him gifts. Wearing his clothes (in your case, you could leave some of your clothes at his place).
posted by yawper at 12:51 PM on April 25, 2018


“Borrow” his jacket and then don’t return it, and then wear it everywhere.
posted by MexicanYenta at 4:45 PM on April 26, 2018


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