Hi there,
I’m fairly new to riding and I recently started going to ride and the place isn’t super big and only has about 20 consistent riders. They seem like a very tight nit group and I’m having a hard time fitting in.
I’m in my 20s and the majority of them are 50+ and mostly women.
If they own their own horses TRULY ADMIRE their horse. I’m in my 70s and that is how I get good vibrations from the ladies in their teens and youthful adulthoods. There is one lady with a wonderful mare and that lady KNOWS how much I admire her horse even though her mare is not a typical hunter/jumper mare.
If they have children or grandchildren keep on asking about them. Older ladies are often afraid of boring their younger friends with the constant litany about how wonderful, cute, artistic, talented and all around wonderful their children and grandchildren are. Be truly interested in their descendants.
Treat these ladies with respect, even if they do not treat you with respect. Right now these ladies probably know more about horses and riding than you do.
Find SOMETHING to admire about the ladies’ horses, tack, training, riding clothes, bridle/saddle/bits. Ladies with horses tend to LOVE talking about them, especially if they are asked questions with true respect for their knowledge.
Sometimes it just takes a while. When these ladies learn how serious you are about your riding you might find it easier to get along with them.
I’m not the best at fitting in myself, but I suggest initiating conversations. Ask them questions - about their horses, their tack, the barn, etc. Be humble, don’t act like you know everything. If you see someone doing a chore don’t ask if they need help, just pick up a broom (or whatever) and pitch in.
You are all just people at the end of the day. Since my early 20s, I would say that the majority of my horse friends and most meaningful relationships have been with people who were 10 to 30 years older than I was at the time. That is still true today. I tend to ask questions about peoples lives, their families, how they ended up with their specific horse or their journey with horses in general. Most people enjoy talking about themselves and learning about other people and I find that conversation tends to flow pretty organically. Also, I think it’s helpful to be sensitive about body language and not take it personally if someone doesn’t seem very open. There are a subset of riders where horse time is truly a space to be quiet and just focus on themselves and their horse. If some of the people are polite, but don’t really seem interested in engaging I wouldn’t make any assumption that it is about you or your age or anything personal. It just may be the only space in their life where they aren’t having to be responsible for other people or managing others emotions and they are trying to hold that space sacred. If it is a lively group, but you’re not sure how to break in you can see if anyone is ever up for grabbing dinner after the barn or doing drinks. Sometimes just sitting around and breaking the ice and hearing other stories is a great way to build a rapport that then translates over to the day-to-day at the barn.
Lots of great posts already!
I would likely start by saying out loud at the end of a lesson with one/some of them something like - I am so thankful I am riding here and getting to ride with all these great people. Thank you for letting me join your group.
Small compliments go a long way. You can almost always find something nice to say about someone/something. But, good advice above, if someone appears to be in their own zone probably best to not interrupt.
The compliment with a question can start a conversation.
I really like your shirt, did you get it at the local tack store or order it online?
You always have the best saddle pads, do they mind if I bring mine own saddle pad to use in lessons?
I love watching your ride, how long have you been riding?
The list is endless.
Do you think the older ladies are okay with a younger male in the barn?
I think the problem is they are used to women at the barn so since I’m a guy it’s more awkward
Bingo.
As a very much older horsewoman, I have no problem admitting much younger men into my horsey circle of friends once they’ve shown me they’re serious about the sport.
Discipline doesn’t matter.
My neighbor introduced himself to me 16yrs ago (he was 24) asking if he could drive his Hackney Ponies in my indoor.
I told him the footing - 3" sand - was probably too deep, but he was welcome to try.
He did, it was, but we’re still friends.
He’s now switched to Drafts, has a 6-hitch of Belgians & I’ve learned a lot about that from him.
Well, I’d be considered old and I wouldn’t care. I wouldn’t give it a thought.
Things are often times more awkward in our head than others perceive them. Just be yourself. If spending time together outside the barn doesn’t feel like a comfortable idea, just do the small things. A warm hello or asking how someone’s ride went goes a long way. If there is someone knowledgeable and you have a genuine question, ask them for their opinion. If you’re riding at the same time as someone consider asking if they want to do a quick bridle path hack together to warm up or cool down.
I am an adult beginner (I don’t think I’ll ever stop being an adult beginner…) who started riding 6 years ago. If you do the math, that means I started riding RIGHT before covid shut everything down. Barn time was limited to 2-3 individuals at a time, boarders got first dibs on time slots, and everyone had to keep their time to 2 hours. I was in an individual lesson (not a group) which was great for learning but not so great for meeting people.
It wasn’t until the middle of the summer 2020 before I started to really ease into talking to people. Our barn really is a close knit “barn family” and so I pitched in with small chores like stacking wood, moving equipment for clinics, and sweeping the aisles. The one question that I found really helped me connect with people was a simple “How was your ride?” and then really listening to the answer! And the next time remembering a small detail when possible to follow-up on when I saw them next.
I will admit, I don’t like talking to strangers and feel uncomfortable initiating conversation but now the riders at the barn are some of my best friends (regardless of age or gender). It’s definitely worth it, but for me it took some time!
Just one opinion, but I wouldn’t try as hard as some of the recommendations above. I would simply stick with cheerful comments about the weather or bugs and “How was your ride?” If you get a “real” answer, then be prepared to pause in what you’re doing and engage in a conversation. As in, “I’ve heard that happens sometimes!” or “I love/hate it when that happens!” Then the next time you see the person, you can ask about it again. If someone has had a difficult ride and told you about it, you can always do something like leave a pack of M & Ms in their locker with a note saying, “I had to buy myself a pack of these because after we were talking the other day, I had a hard ride too; the struggle is real!:-)” or some other humorous note.
As an older woman, who also is busy working full-time, has a family, drives an hour to the barn, etc., I don’t need obvious flattery of my horse or my [cough] riding, nor do I want neediness from my barnmates. Quick questions about trails nearby or different trainers (if an option), etc. are welcomed. If the OP is going to the barn at the same time most days, the OP will likely start to see the same people. If OP is there in the evening and happens to be cracking open a beverage (could be diet coke, could be beer; doesn’t matter) and is holding a six-pack and offers me one to sit and enjoy while watching our horses eat their hay, that would be lovely.
Many older woman do not care whether other riders are young, old, male, female, nonbinary, black, brown, white, blue, green, short, tall, rich, poor, etc. We’re way past all that shit. 
I sure am.
Now this tends to happen on-line, I have told young men that if they have any embarrassing questions the best person to ask is a grandmother, especially one with sons and grandsons. We often have a deeper understanding of males than women who do not have sons and grandsons. On-line, as a grandmother who rides horses, I have answered some extremely embarrassing questions from men.
Young men get embarrassed very easily so this does not happen in person, just within the anonymity of the web.
I am really puzzled how in my lifetime riding horses switched from being an “essential” part of being a true man to a totally useless luxury. When I started ONLY MEN could handle stallions, only men could “break” a horse to saddle, only men were strong enough to halter break, only men could stay unemotional enough not to mess up the horse, only men were strong enough to be farriers or large animal veterinarians and that there were A LOT of horses who only men could ride. This was pretty much universal, it did not matter what way a person rode a horse (English, Saddle Seat, Hunt Seat, Dressage, Western, Western games and rodeo). Back then all the men were assumed to be cis-males, whether they were “he-men” or living proof that cis men can be intellectuals.
I think most young cis men get acutely embarrassed when they land in the midst of women old enough to be their mothers or grandmothers, when the majority of affordable riding teachers are women (or, utter horror, teen-age girls) and they have almost no role models of lots of regular guys being horseback riders. How in the world can they “prove themselves” in front of women who have seen it all and gotten all the T-shirts?
Somehow the Western riders have managed to keep the cis-males, young and old, better than the English disciplines. I have had Western male riders tell me that they consider men who have the guts to gallop fast cross-country and jumping challenging fences as SISSIES, while they, the true he-men “valiantly” crawl around the ring in Western Pleasure classes or shuffle down the trails with their friends.
We need more men riding hunt seat. I do not see how this is going to happen though.
This! And be genuinely interested in their responses. Be engaging and ask questions.
Like others most of my more meaningful friendships that are horsey are with women that were 10-30 years older than me. Looking back on how these friendships formed, they formed by us being acquaintances first and just having casual chit-chat here and there. A good start would be at the end of a communal lesson or ride, inviting them to hack out with you as you cool down your horses.
But remember, for many people the barn is their “down time” and a break away from chores, children, husbands, work – AKA how they recharge after a stressful day… sometimes they just won’t want to socialize and that is okay too, and not a reflection of you or your value as a person. 
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