Reentering the Dating Pool in your late 30s - Guidance needed

November 12, 2016 11:14 AM

After splitting up with my Girlfriend of 8 years over a year and a half ago, I am ready to reenter the dating world. I'm glad that I took time off to work on myself. I instantly wanted to date after breaking up, but it was for all of the wrong reasons. I'm now ready and I need some guidance Details inside

I'm a 37 year old man. I'll be 38 in a month. I have always been in relationships, so I don't have a ton of "dating" experience to begin with. I am also rusty as hell. I have no idea how to meet people or what the general etiquette of dating is.

Meeting people: I haven't had much success with online dating. I'd select the age 28-44 and check off no kids and no smoking. I feel like 28 is probably too young. I look very young for my age. I still get carded. My last partner was 10 years older than me, so don't assume that I am a creepy old guy looking for a young girl. When I was done weeding out - super religious, not attracted to at all, red flags ("all men are liars") or just nothing in the profile other than one pic and a text that reads "looking for a nice guy." There was nothing left. There doesn't seem to be a continuing group of girls joining. This sort of seems like a dead end. There was one girl that stood out. I messaged her and she responded. I responded to that and didn't hear back from her. I assume that she wouldn't reply in the first place if she wasn't interested. I assume that I should just leave it alone.

I don't know where else to meet people. It also doesn't make it easy that I am very particular person. I'd like someone smart and into art and politics and philosophy, etc. Someone with intellectual curiosity and interests beyond reality TV and sports. Someone interested in lots of stuff. I'd rather a cool and smart and nerdy chick than strictly looking for the superficial things such as a perfect body. I know a lot of people that just want someone. Anyone. I'm not one of those people. There seem to be a lot of people that are into "common things" like sports and such. Where else can you meet people and how do you approach them? I don't know how to ask someone out in a museum or the gym etc. What are alternatives to online dating? I've been going to Meetups and even started one of my own, mostly to be social and make friends. There has to be something other than OKCupid and Match. I'm fine with trying different things and getting out of my comfort zone. I know that there is going to be a lot of discomfort, but I am willing to do whatever it takes.


Lastly, some of my friends - females included - have encouraged me to just go on dates even if I'm not too into the person, just to have fun and get laid as well as exercising some of those atrophied dating muscles. I guess that this is fine as long as everyone understands. I've never casually dated or had casual sex (other than a one night stand once). Do people expect exclusivity? Do you just keep going online and looking while dating other people? What obligation do you have? To tell them? I don't want to be a "scumbag" or hurt anyone's feelings. What kind of conversation or understandings are there. There is also the practical matter of STD's. I don't want to be a selfish lover. How do you perform cunnilingus without a dental dam? Just take someone's word for it that they are clean? Not do it at all? I haven't had sex in over a year - the longest since I've lost my virginity. I definitely would enjoy at least having some fun until I meet someone cool, but I'm not even sure how to navigate that. It is so strange how many of these people write in their OKCupid profile that they have sex on the first date. Makes me really nervous about diseases.

I won't overload this post with the million different questions that I have - when you first meet, do you hug? shake hands? I am just looking for some general nuggets of advice and maybe some optimism that I am not going to be able to find what I am looking for.

Thanks a bunch

posted by kbbbo to Human Relations (9 answers total)

Unfortunately, lots of people have switched to Tinder for online dating, which is a terrible system but it's where all the people are now. You may have better luck there than OKC but it'll be time consuming since few people write anything of use in their profiles.

STIs come down to your own personal risk assessment. I sometimes have sex on the first date, I always use condoms for intercourse, and never do for oral. (And I'd opt out of sex with someone who wanted to use a dental dam with me because I don't enjoy it that way, and I expect oral during sex.) I get tested for everything annually and so far I've never caught anything. I always ask people if they have any STIs, but they could lie or not know, so I don't know how useful that is. I only go condom-free if I know someone well and we've both been tested since our last condom-free partner.

Seeing multiple people and then narrowing it down is pretty typical. Dating multiple people longer term isn't unheard of but is less usual.
posted by metasarah at 11:32 AM on November 12, 2016 [2 favorites]

i'm writing in response to your statement "I'd like someone smart and into art and politics and philosophy" specifically.

you will meet these people at academic events and in bookstores and art galleries and waiting for movies and attending art/cultural festivals & so forth. here's my fav technique to ask someone out in the museum or the gym or another social setting where you've perhaps met in person, or seen someone in person, but you don't really know them and you don't have a friend or someone else who can introduce you.

you approach a woman, politely initiate a conversation about anything other than their physical appearance/attractiveness. say something about the art. say something about a workout technique. waiting in line in a cafe? point out a menu item that you love and ask her if she's ever tried it. etc.

if she responds w/ more than a flat, one word answer, generally signaling she wants to chat for a moment, you say, "by the way, i'm so and so, nice to meet you." if she gives her name in response, and are still smiling and chatting and not trying to extricate herself and get back to the art / workout, have as much of a conversation as you can in that moment, depending on where you are and when you get the sense she needs to move along, you say, "i'd love to talk more over a coffee or a drink sometime - here's my card, let me know!" and you give your card with your name and your phone number written on it. get some made and keep a couple in your phone case or wallet, or wherever.

now if you never hear back after that, or if you see her around the gym again and she never calls or texts you, LEAVE HER ALONE. don't bother her again. don't make a point of going over and talking to her every time you see her at the gym. let her make the decision.

why the card? why not something digital? why not social networking? i am suggesting you give the card instead of saying "let's connect on facebook" or similar - or asking her to give out her number, IME this is the most respectful and safe way most women would like to be approached.

it doesn't put pressure on them to interact in the future, or give access to private info, as with adding someone you don't really know on facebook. it doesn't force someone to give up their number right away to a stranger, which a lot of women avoid because we get harassed. it directly signals your interest in a date. and it puts the decision in their hands as to whether or not a date is warranted. it also takes two minutes and is so easy to do in so many places. good luck :)
posted by zdravo at 12:50 PM on November 12, 2016 [26 favorites]

You don't say how large of a metropolis you have to draw upon, but one thing I've realized in a long time of online dating is that a lot of people aren't on it. Think about it: however many you're seeing listed, there have to be more single people than that. Check meetup.com for groups suitable for arts and philosophy types in your area. Are there gallery openings there? I can say a lot about online dating, but it kinda sounds like you'd benefit from finding more community options, from finding someone already into the stuff you're into rather than probing the depth and angle of checkboxes.
posted by rhizome at 12:50 PM on November 12, 2016 [1 favorite]

There was one girl that stood out. I messaged her and she responded. I responded to that and didn't hear back from her. I assume that she wouldn't reply in the first place if she wasn't interested. I assume that I should just leave it alone.

I was you three years ago, and this exact thing happened to me on Match.com... and I decided to message her one last time, just a comment about a picture on her profile (like 'oh, that rock formation behind you is awesome, where is that'), no reference to her not responding or anything, and she messaged back and now we're engaged.

It turns out that women get like 1000x more messages than men do, and many or possibly most of them are terrible. She was overwhelmed and/or discouraged by all these messages and just hadn't responded.

when you first meet, do you hug? shake hands?

It's awkward (for me, anyway) no matter what, so I just let my date make the choice, and it seemed to work out every time. For other 'first' stuff I just asked... like 'is it ok if I kiss you right now?' My fiancee still laughs about it, but for me it took a lot of the stress out of it... I don't want to be kissing someone if they're not into it. Maybe some people can just tell when it's ok, but that's not me.
posted by Huck500 at 1:23 PM on November 12, 2016 [9 favorites]

What area are you in? I think small-town and urban-center have different cultural dating norms.
posted by greta simone at 2:59 PM on November 12, 2016 [1 favorite]

You say, "i'd love to talk more over a coffee or a drink sometime - here's my card, let me know!" and you give your card with your name and your phone number written on it. get some made and keep a couple in your phone case or wallet, or wherever.

This doesn't work. It's vague (never say "sometime"), and it puts the onus on her to take action.

While it is important to be respectful to women you're trying to connect with, you also have to assertive and ask for what you want. Ask for her phone number, tell her you'll call/text, and then follow through. If you want to give someone an out, say "If you don't want to give me your real number, give me a fake one."

Also read Aziz Anzari's "Modern Romance" and this guide.

Getting in to the "dating groove" can take some adjustment, but it's totally possible.
posted by falcon42 at 3:06 PM on November 12, 2016 [2 favorites]

Do keep telling friends you are on the prowl -- I peeked at on-line dating sites and saw absolutely nothing of interest, but there were many friends of friends who seemed to have potential. I (41, happily single for a long time prior) met my partner by accident when out with an old friend who was also an old friend of his. "He's just stopping by to get cottage keys off me," she said, "I hope that's okay. He's good people. He'll just bounce in and out; it won't derail our evening." We chatted briefly and I suggested he had a beer. And that was it. We were quite serious in not a very long time. It was terrific that he was 'pre-vetted,' so to speak -- my friend of twenty years is his friend of twenty-five years, and we had many friends of friends in common; he came with a sterling resumé and I didn't have to waste any time worrying about his being an axe murderer or just a run-of-the-mill jerk; many lovely people held him in high esteem.

Friend generously on Facebook if you're on there, work your social media circles. Go to parties. If nobody is conveniently throwing parties, throw them yourself and encourage people to bring their friends. Make it a goal to meet your friends' friends, and possibly the third circle out there, too. The odds of finding somebody like-minded is much higher, I think. My SO is "smart and into art and politics and philosophy, etc. Someone with intellectual curiosity and interests beyond reality TV and sports." Which makes sense; I don't really have any friends who don't fit at least most of that description...

I am also a fan of brutal honesty. Do not waste time. If you only want a FWB arrangement with a person, say so. If you are so smitten that the only way you want to carry on is if there is a shot at permanency, ask them what they are looking for; weed out dealbreakers ASAP.
posted by kmennie at 6:49 PM on November 12, 2016

I'd select the age 28-44 and check off no kids and no smoking.

This is what stood out to me. You are selecting a range at which most women re-entering the dating market are going to be divorcees, and most of them have at least one kid. You are severely limiting the market. If you're public about this anywhere, even in your match questions, it's also sometimes a red flag even for women who don't want children, because the men for whom it is Very Important that the women not have any previous children often have other issues.

Is this an absolute dealbreaker? If not, I would consider opening this.
posted by corb at 8:47 AM on November 13, 2016 [1 favorite]

Hi, I'm probably in your demographic, 34, single, no kids, no smoking. Those demographics also describe most of my single girlfriends. I've done lots of online dating- Match, Tinder, OKCupid, and lately I've had the most luck with the app ones. In my area, my friends and I have pretty much moved on from Tinder and are now on Bumble. If you only wrote one woman on whatever online dating site you use AND she responded, that seems pretty good.

But I really believe that most connections are made offline. I find that when I'm looking to date, my first step is to reactivate my profile online and go on lots of dates. That allows me to relax in other aspects of my life, and I think it makes me more attractive because I'm not giving off the vibe that I'm desperate. After all, you can't be desperate if you've got 2 dates lined up in the next week! Basically, I go on online dates, many of which lead no where, and try to make more friends offline, which actually leads to dating people. The last 4 guys I dated more seriously I met- set up by my sister, met in a running club I found on meetup.com, met online (Bumble!), met at a party.

Ok, on to your other questions, and this is based on my and my friends experiences.
-Alternatives to online dating- Meetup.com, joining clubs (for example, I just joined a local NaNoWriMo club and a local young professionals group in my field and made a ton of new friends), become a member of the local art museum (mine puts on all kind of cool events and the crowd is always 30-40s, hot and professional). Oh, and definitely let people know you're open to set ups.
- Do people expect exclusivity? Not until you talk about it. I don't tell people I'm dating other people, but I would if they asked. No one has ever asked unless they are asking me to be exclusive.
-Do you just keep going online and looking while dating other people? Yes, you'll naturally stop as soon as you meet someone you like. That's how you know you like them! When you haven't bothered to login to Tinder :)
-How do you perform cunnilingus without a dental dam? Umm.. the same way you did on your girlfriend. Please don't break out a dental dam.
-Just take someone's word for it that they are clean? If you don't believe them, its too early to be going down on them anyway.
-When you first meet, do you hug? shake hands? I usually go for the hug, its a little awkward but so is meeting someone when you've only talked to them online. Just before I arrive, I text what I'm wearing so the guy can be sure he's walking up to the right lady. I also text him where I'm sitting if I arrive first I always say "so nice to meet you" but I say it quietly so the people around me don't know we're on a blind date!
posted by foxonisland at 2:36 PM on November 14, 2016