So im 42, single mom to 2 kids with a pretty demanding job and super contentious relationship with my ex. Im talking 80+ work weeks being my norm for YEARS, and being constantly paranoid of anything i do being used against me in court. Id take ex to court for not paying support and he would respond by claiming i was bad/abusive/whatever. In 14yrs since divorce ive never spent time apart from my kids outside of work/school. Never had babysitter or date – too afraid.
That all being said, ive pretty much only had a couple “relationships” ever, and since divorce with guys who were not local and not an option to have relationship with. I could txt/chat, my kids never knew, and on a rare chance saw these men when i traveled for work and had a bangfest every so often.
About 10yrs ago i logged into OLD which i generally do to remind myself that being single was better than options in my area (im a hard pass on toothless belt buckle sporting guys who live with their mama) and met i guy i thought was cute, had a good personality, and custody of 2 kids of his own about 1yr older than my 2. Ideal right? He asked me out and i panicked. With all the info above, combined with the fact im a girl in IT world and while not a knockout by any stretch i find myself often fending off unwanted attention from awkward nerd coworkers.
I side stepped, and was legit mid panic attack at thought of how i would even go about meeting this guy. I had 2 weekends off per month, didnt feel OK with hiring babysitter and generally worked all weekend when kids were with ex.
Had nothing to do with this guy, everything to do with me being chickenshit weirdo.
We friended eachother on FB (i occasionally post pics for old old OL friends or distant family members) and kept polite tabs.
Eventually he dated a lovely lady and became engaged, then suddenly was single again (they dated 6ish years?)
Id genuinely been happy for him and was sad to hear things went sideways. I loved the fact he never even commented on anything while dating her. Very gentlemanly. We ended up chatting again, flirting, and he brought up again his dislike of chat and deep desire for in person interaction. I think this time he went for softer pitch “we could hang out with kids or you can come over” which i think he intended to be less scary for me but ill be honest scared me more somehow.
I skittered on an answer and true to form he wasn’t willing to continue chat with me and conversation fizzled.
A year or so later, i posted about yet more ex-divorce drama and he reached out offering support and an ear via chat. We talked on and off for a few days and he threw down gauntlet and said “listen, i like you. Always have. But i don’t like chat and my ex refused to have conversations in person and it drove me nuts and im not going down that path again. I want real actual human interaction”
He didn’t make a decided offer and as much as i yelled at my chat “then ask me to coffee you dummy because im a chickenshit” he didn’t and i couldn’t bring myself to do it.
6ish months later he posted about being struck down with the beer flu and recovering i reached out to him and been chatting on/off for the last week or so.
Our first interaction a decade ago he asked me out to dinner if memory serves, but since then its been much more vague upto during covid saying i should come over and watch a movie and i didnt like idea of leaving kids alone for hours (despite being older teens now id never done that) and gave me netflix and chill vibes i didnt know how to handle…
But it seems pretty clear there has been an undercurrent of liking eachother for years. I just dont know if ive blown my chance?
I really dont know how to “date” other than talking online for months and then meeting up and tearing eachothers clothes off. I get very self sabotage in my head. Literally panic mode over what would i even wear? All i own are jeans and nerd tshirts and hoodies, or suits. Lol. Im not even sure what casual dressy clothes look like – they dont live here. How do i handle kids in that situation (tbh they would sell my ass to first guy who offered them a high five)
Dunno. My friends (all male sadly) think im a nut and should just ask the dude out already and stop being self sabotage, but i am worried ive already blown any chance
Help?
30 comments
Tell him a very abbreviated version of what you said here. Tell him you haven’t really dated, especially recently, and you are nervous, especially considering you consider him a good guy and you don’t want to mess up. Don’t tell him everything in here, but definitely keep him in the loop. Besides, you deserve happiness
Honestly after all this….shit or get off the pot. You really have nothing to lose, and everything to gain the way I see it.
I would literally just send him the link from Reddit. I don’t think there is anything wrong with this post, and I think it tells your story in a very concise and empathetic way. It’s not hard to understand how you got where you are or why you are afraid.
Call him on the phone and say “ would you like to go to dinner?”
Please go to therapy. Not trying to be ugly at you but your post has got more red flags than a Chinese parade. Your answers lie within, not from a bunch of strangers on the internet. Please go to therapy.
Sounds like you haven’t seen him in person in 10+ years. You definitely have way too much built up in your head over this. Just ask him to grab a coffee; see if you even click in person after all this time.
With both of you having older teens a hang out that involves the kids sounds… awkward.
You’re the one with the busy schedule, so just ask if he wants to grab a coffee/ a drink on Saturday at 5pm (or whenever the next time you know you have free time is).
I’m assuming that leaving the kids for a short period of time isn’t an issue if they’re in their late teens now, so I don’t see any reason not to give it a try.
After reading this long long drawn out headgame description of yours; I didn’t get one hint at all of what you hope to gain or achieve by meeting this man.
Do you have an idea of what a future or time invested with him might look like if you did indeed decide to step outside your own head?
You are way, way, way overthinking.
You also have an image of who he is, but you don’t know what he’s REALLY like because you’ve never even met. You don’t know if you would even get along well in person.
At this point, either tell him you’d like to meet up and meet up, or stop talking to him…. What do you even want?
Also, I second the recommendation to go to therapy if you aren’t already. There’s a lot for you to unpack here.
Good Lord – just send him a message and ask what is a good day to meetup.
Therapy.
You sound hilarious, hard working, and sassy, OP, a catch in other words. Go for it! Coffee date it up!! If not for him, YOU deserve it after all this time of having nothing substantial for yourself!
Reading this stressed me out. This dude probably feels like he tried everything and you’re either a tease or just not interested. On top of that, the fact that you have these residual feelings that you never act on but are capable of still having a “bangfest every so often” makes me confused on how nervous you could actually be.
Step it up or just delete the dude and start fresh. Already you’re putting this dude up on some weird pedestal by sticking around for so long and having these feelings. It’s just a dude who’s been very upfront with you. You can overthink outfit, if you only have jeans and nerd shirts in your pictures, guess what he’s gonna expect?
So I’ll agree with the rest of the post. Either step up or get out. I’d also suggest finding some way to process some of these thoughts. 14 years and still afraid of dating is a lot of weight on your mind that won’t ever just disappear at this rate.
I don’t know what to tell only that I’m here with you!!! Solidarity sister! Your story is my story and I feel for you. Dating sucks for us single working moms and I don’t think it will get any easier. Take your chance, if it doesn’t work move on. You deserve everything! Don’t settle:)
Take a leap of faith. Put on your best comfy clothes. What will be, will be.
Do you currently/have you had a therapist?
One of your kids seems to be 18 already. Stop hiding behind them. They don’t need you 24/7, you’re allowed to go on dates und could even be a better role model. Stop hiding behind your work.
Jesus, get a grip! You work too much to sustain a relationship and you panic too much too.
You need help, sorry. But leave this guy alone he didnt wait for you, he simply sees your name sometimes online. You should have made time and had a coffee a decade ago.
Ugh “the beer flu” really ruined this for me.
But, anyways… shit or get off the pot… especially if you’ve never even met in person. In ten years. (!!)
80+ hours, plus 2 kids + no help at all? Be real man, this is just impossible.
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Pick up your phone and text him “Hi. I have to be honest, I have been interested in you too on off through all our interactions and I still am, the fear of rejection just took the best of me, I’m not normally a “dating” kind of gal, you know me I work all the time and the thought of actually meeting you is so big that I overthink it. But I have realized if I want something to happen I have to be there for it, are you still interested in a dinner, or coffee?”
You won’t know if it’s screwed up until you’ve showed him clear interest. Take a leap of faith!
Please, for the sake of this poor man’s sanity, tell him you aren’t interested and let him move on with his life
You can’t trust your teen kids to survive successfully long enough for you to go out for a coffee one morning?
Just stop acting like you have. No excuses.
If this man knows half of what you wrote & still speaks to you, cling to him & never let him go
I just need some info before I comment further lol- how close in proximity does this man live to you?
You’re doing your kids a disservice by not taking care of your own needs and happiness. Older teens don’t need a parent around 24/7. Nothing changes in life without a little bit of discomfort. You want change, don’t you? You don’t want to just devote ALL your time to work and serving your kids forever with no companionship, do you? New things are scary and uncomfortable, but so what? Be scared and uncomfortable for one evening. Ask the guy out to dinner. Don’t Netflix and chill or go to his place, go on a real date and fucking relax your neurotic ass down. When you’re old and dying, you’ll wish you did.
First off…is he aware of your time constraints, cause I sure as heck wouldn’t date someone who could maybe, possibly, perhaps see me twice a month. So, even if he does ask you out, when are you going to see him??
I’m going against the grain with this one, I personally don’t think you should date anyone right now. If your not willing to hire a baby sitter to go on a date with someone who likes you, I’d say a companion isn’t even close the biggest priority.
>Id take ex to court for not paying support and he would respond by claiming i was bad/abusive/whatever.
Why not let the courts decide? That’s their job. Your a single mother of 2 that works 80 hours a week regularly. You personally just sound extremely burnt out. I’m a pretty hard worker, but if I’m working even 60 hours a week I’m probably not even going to think about dating and that’s without kids or basically any responsibility.
Gods people can be such jerks here. You’ve got a crap ton of stuff to work through and very little time to do it. Kudos for even staying a little sane with all that going on.
First, I’m hoping that 80 hour week translates to some money. Because you’re going to want to shell out for professional help. No way in hell you want to work through fear like this alone. Take those free weekends and ensure 1 hour of each is dedicated to you getting to feel comfortable with yourself and others.
Next, remember: if someone is consistently into you, it’s you, not your clothes or hair is whatever. In-person could be a total dud as the dynamic really is different… But also maybe not. Both are ok. You’ve been on this long, you can easily survive a dud date and keep the good friendship part.
Keep the ex away from any sound of your dating, but know that simply dating is far from child abuse and he’s not going to actually take you to court because he’ll lose big-time. Having your kids see your navigate healthy relationships is beneficial – how else can they form a picture of what respectful dating should look like? If you’re not bringing home random dudes and neglecting the kids… All will be good.
You’ve made it this far – you’ve certainly got what it takes to go further. Give yourself permission to be confident. And GOOD LUCK!