Tips for the Hopelessly single...And General Romance stuff :)


I’m 42. My last date was in highschool. I’ve only had 3 dates total. The first one I took her to see the Mighty Ducks. the second one with the same lady, I took her to see something a bit more ‘adult’, Captain Ron. The third one, with a new lady, I took her to a local arcade where we played games, baseball, and mini golf. I thought that went far better, but it didn’t go beyond that, and I’m still really trying to figure out why.

Beyond that, I’m SUPER shy. and pessemestic. I’m also an introvert who’s not comfortable in crowds. But once I get to know you, I feel real comfortable in knowing what you’ll be able to take in terms of humor and talks, and start to open up. the problem is, that takes time. and by the time it happens, it’s too late to impress the person and change their opinion.

as far as attempting other dates. I’ve tried. I went to a radio event that was a singles bowling night. there was only one person t here really my age. we became friendly, but she lived too far across the state to even consider a date easy. I became friendly with a nurse at my derm group…after about 5 months of friendly chatter, I decided to get the nerve to ask her out. the look of shock when I walked in the next day practically depressed me for the rest of the week. that was about 5 years ago, and havn’t tried again since.

Murderers in prison seem to have an easier time attracting someone than I do. And the only thing I can figure out is I must be paying for something horrible I did in a past life. makes sense :).

So, I can’t be the only hopelessly single person here. ‘they share a drink of loniness, but it’s easier than drinking alone’ as the old story goes :).

In other random news, I’d date emily or yvonne freeze in an instant. anyone wanna play matchmaker ? :slight_smile:


Dating ladies in HS? You dog. :wink:

Maybe the

category can help you out. A little meetup organizing, a little riffing, and then you’re buying red telephones in no time! Just watch out for that hole in your roof.


I am sure you hear this all the time, and it doesn’t immediately help, but appearing confident will help you a lot. Note I said appearing; you don’t have to be confident, you just have to figure out how to act like you are. It has taken me many many years to get part way there (I’m your age, but I didn’t have dating success until my mid-thirties). Part of it is accepting that you are going to say stupid stuff and do stupid stuff. Let those things you wish you hadn’t said go, don’t stopping talking when you trip over your tongue. You don’t have to believe you are hot poop, but it helps to act like you know (not think) you are. When in doubt, ask yourself what Liam Neeson would do. Do that, just without threatening or killing anyone.

Another thing people probably tell you is that it is a numbers game. It is somewhat true: you have to ask out a lot of people, and you can’t let rejection stop you. Remember that rejection is almost certainly not about you: everyone has tons of stuff going on, and most of the time you are just a tiny blip. Obviously you don’t want to ask out everyone, but you need to kick around a little and see if you get your foot in a door.

Timing is super-important. If you have waited five months, the person you are interested in has probably decided you aren’t interested. In many cases, you have a few minutes upon introduction to get yourself on someone’s possibilities list. That means being a little bold. You don’t go all Pepe Le Pew, but you need to make it clear that you are interested. People don’t want you to hesitate, they want to see themselves as desirable. If you don’t indicate your interest, why should they go out of their way to engage you? Putting yourself out there is pretty much a requirement: if you aren’t willing to put your pride on the line, why should anyone take your interest seriously.

Important things to do: listen actively to everything they say. Don’t be creepy, but try to engage them on the things they say to show you are listening. People love to talk about themselves, make sure your potential date gets plenty of chances (which also gives you some good intel… keep your memory sharp). Make eye contact, and don’t look away until they do. Smile. Make sure your body is faced square towards them when you talk to them directly, keep your chin up and speak clearly. Feel free to follow the Obama Rule: you have the floor, you can draw out what you are saying or pause to regroup in the middle, as long as you don’t wait too long (I believe the limit is four seconds, according to recent science). If you say something silly, laugh it off and immediately forget it, unless you can turn it into a joke.

Finally, I suggest trying online dating. The aps are crappy, and the scene is unpleasant, but if you get a date online you are guaranteed one thing: your date knows you are interested and is at least a little interested back. That can be a huge huge advantage for a shy person. Trust me, I know, I was very very shy when I started. Honestly, I only rarely get dates from meeting people in person; online simplifies the numbers game a lot.

I hope this helps.


I tried online dating for about a year and a half. both paid and free sites.
Sent out about 50 messages, and only received one response back saying the person was no longer available (yet their profile didn’t reflect that, go figure). So, I figure online dating wasn’t for me either.

I’d feel much better if someone recommended someone to me. I know they know me, I know they know the person they are recommending. but that usually doesn’t happen because they are probably afraid of it going sour and loosing a friendship.

I decided recently to take that advice of not waiting a long time. I met a lovely lady who worked in the office next door to us, that was renting from us. I told myself that the third time I saw her, I’d ask her out. but she got fired! The company downsized it’s employees! I mean, if that’s not something working against me, I don’t know what is :).



You could base a strategy around the old sitcom joke that goes like “I’m going to marry the next person that walks through that door”. Just make sure you aren’t in a sitcom though because the punchline is incoming.


Good recommendation, and I’d also mention this Facebook group:

I haven’t been in it myself but it seems like a good place to meet someone with a baked-in common interest.


I’m in a similar situation, but in my case, there’s an added fillip of religion (meaning that I am very religious and my beliefs are a major part of my lifestyle). However, I can’t really help you figure out how to solve the problem. Part of the reason for that is that, while in an academic sense, I can see the advantages in being in a committed relationship and being married, I’ve never actually felt genuinely attracted to another person. I’ve been on dates (most recently more than 10 years ago), but only in a friendly sense, not in a courting sense. It’s probably not true asexuality, but there’s a time and place for going into those kinds of details and this is likely not it. :slight_smile:

So good luck and maybe some of the suggestions others are making will help you.




I’m using it as a noun, definition 2c. :smiley:


Well that’s Fillip’d Up :stuck_out_tongue_closed_eyes:
To add something relevant to this here thread, I was pretty much single until I got married at 31 back in 2001 and it lasted 4 days shy of 16 years due to her passing from uterine sarcoma on January 10 2017. a few months later my new wife found me from of all places, YouTube. She was a recent fan of my channel of my random vlog and project videos and we talked for over a year before we actually met in person. She lived in Pittsburgh some 500 miles away but we didn’t let distance stop us from coming together. She flew down for my birthday in June 2018 and we hit it off and got married July 3, 2018 after my job interview with the USPS. She sold her house and moved here with me in October, 2018 and she’s been here ever since. I wasn’t even looking for another relationship as I was still recovering from the loss of my first wife and really needed someone to talk to instead of talking about what I was dealing with to anyone out there watching my videos.
I guess my point is that things happen for a reason; what ever they are we may never know but love will find a way but maybe just stick to talking with someone for a while and see where it goes but don’t give up. Just my take.


I have :). Unfortunately, it was also the first person I met that I felt the deepest connection with :). Only one or two others came close :).

Sadly, my story with her ended with a ‘lost her for all time’ speech :slight_smile:

We’re still great friends, and I think she appreciates me more now, ironically, that she’s a little older as I matured way faster than anyone else I knew. but the only way this story has a happy ending is if she gets divorced and I wouldn’t wish that on anyone just to make me happy with a second chance :).

so, back to square one :slight_smile:


I am not the person to ask for tips…I can’t flirt my way out of a paper bag, I overthink into paralysis when I’m attracted to someone, and the three people I’ve met in my life that I could see myself in a relationship with…were not attracted to me and we just became friends. :woman_shrugging:

And good gods, I do not have the time or mental bandwidth to try the dating scene. :face_with_spiral_eyes:

(To be clear, I’m pretty okay with this. Would I like a romantic partner? Sure. But I’m not going to drive myself to distraction trying to find one or settle just to be in a relationship. YMMV.)


I’ve been stuck in the friend scene too. perfectly fine with that, but gets frustrating after a while :). especially when you see other folks who you’d think would have a tougher time finding someone, finding someone far easier.

all inall i’m happy being single, more or less. but I WOULD like to give the married life a try to see if I’d be any good at it. having someone to rely on and support you as you support them must be a great feeling :).


I’ve been single so long I can’t fathom being in contact with another person for very long anyway. I like to think of myself as the stoic type…


I understand that. I have several friends who are poly, and I tease one of them (who is a very good long time friend who has a husband, a girlfriend, and a boyfriend) like “Dang, I can’t even get one!” :joy:

I suspect I’d make someone’s perfect partner, but darn it, I wish they’d just figure it out and call me already! :rofl:


The silver bright lining side to not sharing a living quarters is that nobody is throwing away all your cool stuff.


It sounds good, but multiple partners is a real job, as I’m sure your friend knows. From my experience it can be rewarding, but exhausting. I knew a lady with four boyfriends and everything in her life was rigidly scheduled to make sure she got time with everyone.


Oh, I can imagine! I respect anyone who makes the poly life work, and through my friends, I see just how much work and communication it takes in a polycule. And boy, I know it’s not for me. I have enough birthdays I have to remember. :partying_face:


at this point, with almost everyone married, might have to hope that becomes more normal heh.


Take a look and see if there are groups or meetups close to you that share an interest you have. It could be something you’ve always wanted to learn more about or something you know like the back of your hand – it doesn’t really matter because the point is to go and meet new people. Having the shared interest makes sure everyone has at least that thing in common, and having activity or things to focus upon is helpful if introverted or where long, idle bouts of being immersed in other people is draining. Keep things laid back and fun. The key, really, is to go and keep going. Give people the time and opportunity to get to know you.

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