In the green flag post that I made there was a mention of a date idea pool. A couple of people asked for it to be made into a post. So, I thought I would do just that. I think there should be a little more than that though. We should add in our experiences (good or bad) with certain dates, and we can ask about dates we haven’t done.

My (36M) perspective will be slightly off compared to most in here. I’ve spent almost my entire adult life in LTR/Serious relationships. I was married for 11 years and am recently out of a year long relationship. I’ve never OLD and have never gone on a date with someone I hadn’t met IRL. I’ve only been on dates with someone I had some chemistry/rapport with. My view of dates will be reflective of that. I can’t relate to feeling the need to have a bailout plan on a date. I’m a huge fan of outdoor activities.

Dinner- This is my go to for new dates. It’s a classic for a reason and makes for an easy time to talk. I tend to choose quiet restaurants. After a few dates I really enjoy having them over and cooking for them.

Coffee/Drinks – I have a crepe place that serves amazing coffee close to me. I love going there as a date. I’m not a big fan of just coffee/drinks. It feels a little too impersonal for me.

Vineyard/Picnic/Park – This is my favorite. I love to pack a lunch, go to a vineyard, and wine taste. You can do it at a park as well. I also love going outdoors after dark and laying down on a blanket and looking up at the stars. (I’m a hopeless romantic)

Winery/Distillery/Brewery – I enjoy going and doing tastings at a place. Different verses a Vineyard as I usually won’t pack a lunch. I probably wouldn’t do this for a new relationship. It’s too reliant on them enjoying tastings.

Museum/Art gallery/Botanical gardens – This is something I would definitely not do with a new relationship. I wouldn’t do it as a romantic date either. I find it is a very niche thing to do with someone that is also into this kind of stuff. I really enjoy these events though and find them quite interesting. The one exception would be Christmas lights at a botanical garden.

Hiking – Absolutely love this one. Of course, you need a level of comfortability with the person for them to do it.

Comedy clubs – A really fun night to build upon attraction. I’ve found every time I’ve done something like this, I left feeling closer to them. There’s just something about laughing with someone that I love.

Golf/Mini-Golf – I absolutely love golfing. I’ve never taken a date though. I have taken a female co-worker with me once and we had fun. Although, it was a group, and she knew one other person. She didn’t play just drove the cart. I’d be curious what others feel about this. I’ve notice someone every now and then out as a couple and they rarely look happy.

Top Golf/Bowling – Similar to the last, I’ve only been in a group. I am very hesitant for the same reasons. Every couple I see doing this looks miserable.

Painting/Arts class – This is something that I’ve never done with a date but am very interested in trying. I did it with my sisters and had an absolute blast.

Broadway/Ballet/Opera – Absolutely love this one for a serious relationship. Who doesn’t love getting dressed up and going out for a romantic night.

Escape room – I did this with a somewhat new relationship and had a blast. It is definitely a somewhat niche thing that I could see backfiring. I wouldn’t do it with just anyone.

Ziplining – Absolute blast, I highly recommend it. It’s a very fun date experience.

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Thats my main list of dates I enjoy doing and others I’m curious about. Would love to hear other people’s experiences with types of dates.

19 comments
  1. You have some great ideas there. I’d enjoy all of those except the golf one!

    The third date I had with a guy we played raquetball at his gym and that was really fun.

  2. Well I really dislike dinner dates (I get really anxious about eating in front of someone, it can get awkward just sitting there trying to make conversation, etc), I absolutely love museum and botanical garden dates (and have been taken to each as a first date and had a great time), distillery/brewery dates are a no since I don’t drink, I have done mini golf, Top Golf, and bowling as dates before and they’re pretty much my favorite, I love an active and competitive date.

    I would add to the list: axe throwing (another fun, active, competitive option), walking around town (with or without dogs), dancing (can you tell I really love active dates?), fishing, cooking class, visiting local tourist traps, or roller blading (ice skating even better if you have a rink!)

  3. You have m great ideas… as a female I prefer the first 2-3 dates to be away from my house or their house. Usually somewhere in between us or in the city.

    The amount of first dates I’ve been offered that end up being just down the road from the guys house- feels like low effort and just a ploy to get me back to their house…

    I feel like active and fun dates are great for building chemistry and a great way to do things you enjoy with someone.

  4. I had a few VR dates during the pandemic when everything was closed. Those were always fun🤣

  5. I love playing bar games on dates- darts, pool, shuffleboard, cornhole, etc. it’s low key but can be a lot of fun.

  6. Personally I think that OLD has added a date before the “first date”, which is why I’d prefer to not get dinner with someone I’ve never met IRL and would rather just grab a coffee and go for a (non-strenuous) walk or grab a drink.

    The date ideal pool is great though, I freeze up when it comes to suggesting date ideas. Will definitely use this for dates 2 through to infinity.

  7. Zoo is one of my favorites, because at least if the date is a dud, I got to see otters and capybaras. I did a murder mystery jigsaw puzzle on a date (not the first) that was fun, and also bubble tea is good alternative to alcohol or coffee. Also had tea and scones on a date once, which was different. I could see Apple/berry/fruit picking being fun for a few dates in (then making pie!)

    Edit: date being a dud, not a dude, though sometimes they’re both!

  8. Escape rooms are the pro move for dates if you want to determine if you have good communication compatibility. I broke up with someone after he pissed me off at an escape room, it was a straw that broke the camels back that I couldn’t look past.

  9. It might sound silly, but the arcade is my favorite first date. Play some games, let loose, see how the other person is under pressure when playing time crisis or house of the dead.

  10. Disagree about museums/galleries. That’s a SOLID first date and my usual go to. I live in DC where there’s a ton of free museums and usually a bar within a short stroll from any gallery if things are going well.

  11. Kite flying! I’ve done it both with fancy kites and with kites we picked out together at the dollar store. Both super fun dates.

  12. Flea market

    Can connect to each others hobbies.
    Lots of things to talk about

    Top tip – have a competition on who finds the most laugh inducing headwear and buy one for each of you. Take pictures in the headwear and go for tea and biscuits in said headwear, act “prim and propper”, make up histories about how you aquired the amazing headwear and so on. the one who laughs first buys the other one a icecream.

  13. They’re all great ideas, I’d probably add I guess brunch is another idea. Also going to theatre and watching a lovely musical. Also going to the markets like food ones or small cultural festivals generally. Concerts are good too, there are some you can sit at and enjoy the music. The opera is another pleasant event to watch and do as a date as things progress. Also you forgot cooking, cocktail making and art classes like pottery.

  14. I can’t really provide perspective as I’m in the same boat as you (recently separated after 16 years and have never dated in this new dating world). But I wanted to add another option mainly so someone gets to do it, if not me 😅. A football game. The FIFA World Cup is coming up and if I was ready to start dating, going to watch a game together at a cafe, bar, or outdoor area that was showing it would be ideal

  15. Playing frisbee in the park, or going swimming.

    Dinner dates, musicals, botanical gardens, etc. are too expensive just to see if you like someone. Those things can be done after there is strong attraction between both people.

  16. Some unique/memorable dates I’ve had are: whale watching (plus it’s fun to go out on a boat), destruction room (basically you gear up and smash things), rock climbing, axe throwing (although it gets old very quickly), food truck festival, board games at a park, wine tasting safari in Malibu, Halloween night at a theme park, outdoor movie showing

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