Middle-aged guy trying to date in NYC/DC. What am I doing wrong?
November 6, 2017 7:10 PM   Subscribe

Like the title says: I'm a middle-aged guy trying to date in New York City or D.C. Hope me, datingfilter! Snowflake details after the jump!

I'm 40, a year out from my last serious relationship. Without getting into details, it was a serious enough relationship (we lived together) that I thought it merited me spending time out before jumping back.

Things have changed since I was last out and looking, though! And though I make it a point to "swipe right" on lots of people, and craft brief yet thoughtful messages to people I like, I'm not getting anything back. Like...nothing. To the point where I'm wondering if I'm doing something wrong, because the few people who do pick me aren't people I'm interested in. It's at the point where it's affecting my confidence. I'm under no illusions over how much online dating sucks, especially for women. And I realize that I'm probably not the pick of the litter, especially at my age. But still!

You can see my OKC profile here. Feel free to critique it, give me tips, what have you. MeMail is fine!
posted by arkhangel to Human Relations (22 answers total)
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posted by atomicstone at 7:18 PM on November 6, 2017 [2 favorites]

Profile seems good as far as I can tell. I'm a bit older than your demographic but you seem completely AOK to me from your profile and I'd introduce you to my sister if you lived in MA. That said, you probably want more to make it pop since everyone's an online dating expert lately it seems.

- I would lead with the colorful smiley picture, it's good. The one you picked may look more like you but it's not as flattering. I like your choice of photos generally, I think they do a great job at telling a story. Politics, army, cats, family, you.
- I would skip the Trump thing in the opener because you basically mention that later in a funnier way. I'd also skip the self-deprecating Jeopardy thing and just mention it without the "didn't win" stuff
- If you are a person with a good sense of humor, I'd include more of that
- I think the six things section is strong and the "really good at" section maybe needs to be used as more of a thing to show off your personality. Are you in a certain online trivia league?
- same with keeping things positive. "Rather than specific foods, I like different cuisines. Say: Korean. Or Italian. Or Vietnamese." Just say the last part, not the first part
- "soft touch" seems a little odd, it could mean that you're a pushover, might want to rephrase that.

Also nothing you can do about this but you are on the short side for dudes. No big deal but that might be part of the mystery since you may be starting from a smaller pool. Also, are you really average build? You look like you might be heavier than that. Which is fine! But might want to have a photo that is a little more recent and revealing. There is a wide age range (I think?) represented in your photos. If I had a photo of you with a cat, I'd include it. I'd also put captions under all your photos not just the DNC and family ones.

I think it's a solid profile. I think if it were me I'd also be getting out to trivia events (you probably are) and mentioning you're available. As you know, a lot of this is a numbers game but I think you're starting from a solid footing.
posted by jessamyn at 7:36 PM on November 6, 2017 [6 favorites]

I live in nyc and I’ve stared at a million okcupid profiles in your age bracket so I’ve seen your competition. Your profile is pretty great! But your photos need a little work - your first photo makes you look a little scary, and on the second one, your glasses are too small. But the smile and lighting are good! Could you take another like that but with your bigger glasses?

One cat photo only, take out the sister and grandma photo. Do you have any photos of you that make you seem really fun and sort of goofy? Right now your photos are mostly sort of neutral, but your profile reads as you being fun, so it feels like two different people.
posted by umwhat at 7:45 PM on November 6, 2017 [3 favorites]

How many messages are you sending out per day, on average? Can you give an example or two?

Profile is not viewable if not logged in..

Yeah, OKCupid changed something moderately recently and now you can't see profiles unless you have an account with them.
posted by Slinga at 7:48 PM on November 6, 2017 [1 favorite]

Response by poster: @Slinga: I only message people I'm interested in, and I don't message everyone I'm interested in, if that makes sense. I'd say probably about 4-5 messages per day? Example:

Hi! I really liked your profile, especially the part where you mentioned meeting a moose (I’ve met one)…and the part where you said that online dating platforms inhibit our capacity to *be* with other people, rather than offer up a carefully modulated facsimile.

OKC thinks we’re a great match, so I’m writing you. Hopefully you’ll write back; I’d love to get to know *you* better.

I don't know, maybe I'm doing the messaging thing wrong.
posted by arkhangel at 7:54 PM on November 6, 2017

Response by poster: @umwhat: made the changes you suggested! I'm due to get new pictures this week or next, so I'll update my profile with those pictures. :-)

I don't have many pictures of me being goofy, because I'm not one to have pictures taken of me? But I'll see what I can dig up! Thank you.
posted by arkhangel at 7:57 PM on November 6, 2017

OK, with your example, I think you need a little more meat to your messages. I thought the first section was fine, but the second part "OKC thinks..." can go. Ask a question about something in their profile, go into more detail about your moose, go into more detail about online dating platforms, etc. Not necessarily all three of those, but something solider.

4-5 a day is a pretty good number, and I'm surprised you're not hearing back more. Realistically, though, a lot of women on OKC are just getting deluged with messages, and even if the majority are one-liners or just one-word messages, it's still hard to be seen through the deluge. Keep trying, and good luck.
posted by Slinga at 8:02 PM on November 6, 2017

Add more to the last 2 questions in the profile. It starts off nicely and then feels like it ends a bit abruptly. You seem charming and totally date-able, though!
posted by pseudostrabismus at 8:03 PM on November 6, 2017

Response by poster: @pseudostrabismus: thank you! I made the changes you suggested. We'll see if it works.
posted by arkhangel at 8:14 PM on November 6, 2017

You don't mention how long you've been on OKC, but I know in my first 2-5 weeks I would read way too heavily into my first interactions (or lack thereof) as bellwethers of my Entire Future Dating Life Forever. If you're still in that time period I think the best advice is honestly just, like, keep your shoulder to the plow while things coalesce a bit more. No need to reinvent the wheel continually. I know that I had a years-in-the-works mental model of how Online Dating was gonna work, and it took a little adjustment period to get in line with reality.

Anyways my situation's pretty similar to yours (straight dude, long past my twenties, also just trying out online dating for the first time). So hopefully my 2c is helpful even if I'm not your target reader.
  • Seems to me like you have lived a MUCH MORE INTERESTING life than me / most people and I think that will draw more interesting people to you. The more you can front-load that, the better, I think!
  • Smiling in your first picture is good! I wouldn't jettison the B&W one entirely (it's a sharp photo!) but to avoid coming off as overly stern I'd lead with the 2nd one (or even the 3rd w/ Trebek! see previous note re: interesting life)
  • MAYBE IT'S JUST ME but I've read the phrase "like to laugh" / "love to laugh" on so many profiles at this point that it's hard to stop my eyes from rolling backwards into my brain whenever I see it. The sentiment's great, but I think any other choice of words works better for me -- or even better, just "show, don't tell" and let your sense of humor come naturally through in your profile. Honestly, at this point if I was reading someone's profile and they said "I hate to laugh" I would actually laugh, and message them.
  • Get a picture of yourself holding the cat instead of a picture of just the cat. Mostly because it puts you into a viewer's awww-cute-cat thoughts. But also because rules-sticklers will eventually report a picture as "NTU" (not the user) if you're not in it, and it'll get taken down. But mostly the first reason!
  • "Let's do this in person" is not a bad way to close your first section but it might come off a little... demand-ish? "Let's do this in person :)" or "Let's do this in person!" sounds a lot more spritely and inviting than "Let's do this in person."
  • Best advice I've got: you only get better at this shit by failing at it. Fail often! Keep failing! Hang in there!

posted by churl at 8:15 PM on November 6, 2017 [4 favorites]

The thing with messages is that you have to make them easy to respond to. Your message is perfectly nice, but what does a person say in response? You say you'd like to get to know them better, which is great, but presumably you're not expecting them to respond with a description of their personality. You gotta ask a question to open up the conversation. Even if it's just "I've met a moose too, didn't you think it was [insert idiosyncratic detail about moose meeting here]?" Otherwise, if I got a message like that, I might plan to respond to it but never get around to it because I'd be trying to think of something in particular to say and then life would get in the way. Online dating is already exhausting; I think you get the best results if you make it easy on people.
posted by sparrow89 at 8:23 PM on November 6, 2017 [6 favorites]

I guess you've been making changes as you go, and at this point, I think it's really good. I do think better photos couldn't hurt. I really like the one where you're taking a photo of someone else, but the one that's currently your top one is a little stiff and doesn't convey your positive energy the way some of the others do. And the part where you talk about liking books started to drag on a bit. (Maybe mix up the sentence structure a bit to have fewer that start with "I love...") But mostly, I like the unbridled enthusiasm and wouldn't lose too much of it! Also, I like "soft touch." To me it conveys confidence matched with thoughtfulness, not that you're a pushover. Anyway, fuck the haters* is what I'm trying to say. (*if there even are any)
posted by salvia at 8:41 PM on November 6, 2017

Also, try asking a question in your messages. Instead of just saying 'hi I like a/b/c about your profile' or whatever. Ask a follow up question. Start a conversation.

"Hey, so how was it that you've met a moose? I've got my own moose story too!

I found the part where you said that online dating platforms inhibit our capacity to *be* with other people, rather than offer up a carefully modulated facsimile, to be really interesting. Do you think we're just dooming ourselves, or that it's our best chance for trying to find a partner in this technologic age?"

Then, "Hi my name is...XYZ"

Questions. Questions are key.

Give her a chance to follow up. If she does, continue the conversation, maybe with a few more questions based off her response, then end with "I'd love to chat further over drink/coffee/walk in the park/etc if you'd be interested. You seem really rad/interesting/charming/etc".

And yes--don't say 'love to laugh'. It really is an eye-rolling cliché at this point. Also, no variations like 'like to have fun'.

Good luck!
posted by greta simone at 8:57 PM on November 6, 2017 [1 favorite]

And I realize that I'm probably not the pick of the litter, especially at my age.

This, right here, is the attitude that gets you nowhere and permeates your interactions with others and, without having read it, perhaps even your profile. The implication that there are men out there who are so universally good looking that they just need to snap their fingers for women to fall all over them is delusional at best. And if such men exist indeed, all they have over you is confidence.
posted by Kwadeng at 10:33 PM on November 6, 2017

And I realize that I'm probably not the pick of the litter, especially at my age.

lord help me I'm going to make a sexist generalization. my first ever, so please evaluate it generously as it is the work of a beginner. here goes: women in their late 30s and early 40s DO NOT WANT TO KNOW THAT THEIR MALE PEERS FEEL MIDDLE-AGED. if you want to date a sober, responsible, and realistic woman who has her feet firmly planted on the winding road that leads towards certain death, she probably won't mind. and it would be sensible of you to want that. but like

if you're middle-aged, so is she. and while self-deprecation is underrated and I like it, and I enjoy unhappy men as much as anybody, being depressed about your age is the most contagious kind of depression and the worst kind to joke about because it never sounds like a joke. lock that insecurity up in a silver casket and drop it down a well.

as to the profile, there is nothing terrible in it. you sound more sincere than I favor (but most people like sincerity) and I am dismayed but not surprised to learn that 4-5 new message recipients per day is considered selective for men. I believe you are probably way more selective than the average, but while it's great you're finding that many people you really like, you could cut that way down and make your messages less template-like. not longer! just more aimed at starting a specific conversation.
posted by queenofbithynia at 10:49 PM on November 6, 2017 [9 favorites]

You have a really good profile! Only a few subjective things strike me as a reader.

First, it sounds like you've done extremely cool shit in your career, and I feel like your profile is peppered with relatively random clues about that (Situation Room mention, DNC podium pic, etc.) rather than just clearly stating you've had your hands in some really exciting pies. That's a tough line to ride and I can tell you don't want to seem arrogant. But maybe you can find more confidence/straightforwardness in talking about those experiences – they make you interesting and set you apart.

(And this is very subjective, but I'm not sure about the cat picture. It's a beautiful photo and of course she's still a big part of who you are. But the sadness of looking at the caption and thinking "Oh no, poor kitty" may be an odd thing to navigate for readers.)

A few other details:

1) One thing that leaped out to me is that your location is set to Manhattan but you live in Astoria, based on your first sentence. Unless I'm misreading, that needs reconsideration. I think you've got the value equation wrong there (I think the advantage of being in "Manhattan" for searches [if that's your aim] is far outweighed by the disadvantage that to many women, getting the sense that a guy is fibbing details to look better is a major turnoff).

2) Making your first few sentences engaging and crystal clear is really important. I had to re-read and pause to get the sentence "Reformed political operative now doing IT security after 2016." (At first, it read as oddly constructed and a sign the profile was out of date – it read as saying you will be doing IT security as of 2017, rather than saying you left political work as of the 2016 election.)

3) I really like that you have earnest, non-stunt, non-cliche answers to most of the questions. The ones that need attention are the Friday nights one (currently the same answer as so many others give) and your "most private thing" (it's a cliche and for some a turnoff to answer that question with a humblebrag – the bit of info you have there is really cool, it just could fit better elsewhere).
posted by kalapierson at 4:18 AM on November 7, 2017

35 year-old single woman in NYC here, who has slogged through hundreds of profiles and now makes snap judgments after doing a quick flip. Here are my comments:

- I'd lead with the paragraph that starts "Love talking about politics..."
- Take out "Let's do this in person." I see stuff like that and it reads as laziness, especially when accompanied by little text or boring text. We all know it's an imperfect medium. I took the time to craft something interesting and thoughtful despite that, why shouldn't you?
- I don't see 'Working on space camp' or 'Dropping out of space camp' very often, but it's usually from dudes who have something to hide (they mention nothing about their career or are doing something like playing in a rock band full-time). Did you do that because you don't have a bachelor's degree? You seem to have a great career (the Situation Room! What!) that you take seriously, and you enjoy intellectual pursuits. The Space Camp thing overshadows that.
- Your six things section borders on boring. Definitely take out the IPhone. The others work when you get specific with it. You play the violin? Whoa, cool! Art? Yeah, yeah, we all go to museums. (Maybe talk about how often you go or your favorite styles or something.) Is the cat in the picture yours? Mention your cat!
- In your spend a lot of time thinking about section I find this sentence patronizing: "It's OK to be worried about it." Um, I know that, random Internet dude.
- Typical Friday night is boring. Yeah, I know, we all tend to chill on Fridays. Yeah, I know, no one has a typical Friday night. Give a an example of how you chill after work or of what you do on a Friday.
- Please don't take this next one as a personal insult, but this is exactly what goes through my head when I check the desired age range: You are 40 years old. You want to date women 12 years younger than you but only five years older than you. Gross, dude, especially considering that you are no prize pig yourself. Oh yeah, you totally like "strong women." Give me a fucking break. I don't care if it's true, I would balance the age range.
- This leads me to uncharitably ask...are you messaging a bunch of 28 year-old women? I'm not saying you couldn't date a 28 year-old, just that OKC and NYC are a bit ruthlessly looks obsessed, and a touch of realism might help your chances. (Which might mean either messaging a different set of people or working on your own personal fitness/style).
posted by unannihilated at 4:54 AM on November 7, 2017 [18 favorites]

Forty is not middle-aged!
posted by amro at 5:50 AM on November 7, 2017 [1 favorite]

36F, met my husband on OKC in 2012.

One thing I used to like in a message was a reason the guy thought I might like him. It's a less common tactic than "pick a thing in her profile, and comment on it or ask a question about it," and it shows you read all the way to the bottom of the profile, to her "looking for" section or whatever it's called. i.e., if she mentions she likes guys who are x, y, and z, mention in your message that you are x, y, and z. Also, if she mentions she likes guys who are vastly different from you, maybe you're not a match. My profile clearly stated what I was looking for (I believe I had something about preferring sincere people to sarcastic people, and intense people to laid back people, and also that I was unusual in that i vastly preferred short guys to tall guys*) and I was always so annoyed when guys who were the complete opposite--self-professed laid back, sarcastic guys who were 6 feet tall--messaged me and didn't even acknowledge my stated preferences.

Another thing I used to like is a direct, but not-making-plans-already request for a date in the very first message. "May I buy you a drink sometime?" is a good one.

*Don't let the height stuff make you feel bad. It is true that there are tons of women out there who are height-ist. There are also tons of women out there who are a smidge over five feet tall and who don't want to feel like a child next to their mate. I'm one!
posted by millipede at 7:50 AM on November 7, 2017 [1 favorite]

I was wondering about the age range thing myself, as someone not that far from that age myself, who's been dating on OK Cupid in NY recently (I've got it turned off for now). I'm less fussy than unannihilated -- your age range doesn't look gross on its face to me (yes, unbalanced, but at least you include women a fair amount older than you are). But if you're consistently only messaging significantly younger, that might be why you're not connecting.

If you're not doing it already, try messaging some women exactly your age and older? See if that gets you better results? And your profile looks really pretty good to me. There are things I'd edit, but nothing that I think would make a significant difference.
posted by LizardBreath at 10:37 AM on November 7, 2017

Response by poster: Everyone: thank you for your advice and contributions. I really appreciate it! I'll update this if anything changes. :-)
posted by arkhangel at 12:26 PM on November 7, 2017 [1 favorite]

One more thought, and I'm not sure if it's cheering or the reverse. But it's a very likeable profile in a MetaFiltery kind of way, which means you sound way over on one side of the spectrum for being sort of clever and literate. This is a good thing, but it's also a specific thing -- that is, you might be looking at a longer, slower search process because there's a particular, smallish segment of the population that's looking for MetaFiltery types of people? Not that I have any solid idea what I'm talking about, not having gotten much out of OKCupid myself.
posted by LizardBreath at 1:37 PM on November 7, 2017 [1 favorite]

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