Pengworm

Did I get asked out? Warning LONG

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So I had surgery this past September and have lost around 80 lbs from then and 110 or so from my highest weight. I also have been going through a seperation amd divorce from my husbamd of fifteen years. After being together since we were teenagers for literally our entire adult life ue completely changed and was cheating. I hadn't had feelings for him for years even before any of this happened I was longing for a relationship with a connection we no longer had but never pursued anything. 

About five or six years ago when I was at my biggest there was a cute young guy at work that I got along with really well. He would always flirt with me but I figured he was just being nice because why would a 20 year old be interested in a fat thirty something married mom? One night when the roads where bad he asked me to stay with him instead of going home and I again laughed it off. He left our workplace about four yeas ago but stops in and says hi whenever hes in town over the years

So fast forward to a week ago. He hadn't seen me since I lost the bulk of my weight. I truly look like a different person. So while Im working he came and talked to me. Told me how gorgeous I looked and omg I had really lost a lot of weight I thanked him. He asked about my life I told him my divorce would be final next month. He looked ver confused. I thought that I had told him prior but I hadnt. So he stands there for a minute and says "Does that mean you'll finally flirt back with me now?" I akwardly laughed it off. He continued to compliment me and walked with me as I was leaving. We talked about a mutual friends wedding coming up next month amd he said he should be my date. I akwardly laughed that off too and said I was going with a girlfriend. He stood by the door amd kept talking and said we should go get drinks sometime did I like pina coladas. I didnt know what to think and akwardly said something about my kids who had just texted me. He asked about them and said he couldnt believe how old theyd gotten. I told him I really had to go but it was great seeing him. 

I have been saying for a couple of months to my close friends that I am so ready to just date for fun. Nothibg serious but I'd love to go out and have fun and make out. I am looking and feeling great and am ready to have fun. So I tell my friends about this exchange with this guy amd they tell me I am crazy amd why didn't I give him my number and take him up on his offer. I told them I just figured he had to be joking or there was something wrong with him because he also flirted with me when I was fat. Why would a very cute guy 13 years younger than me be flirting with me now let alone when I was huge? My friends told me again I was dumb amd that he was always a nice guy and probably just actually liked me for me. I still think he must he nuts or have a fat older woman fetish or something. However the more I thought about it the more I thought we might actually have fun together just grabbing drinks so I fb messaged him and said hey I thought about it pina coladas sound good so get ahold of me the next time youre in town. He responded right away with "lol I will." Wth does that mean? Then I asked him if he had snapchat and he said he did. I gave him my username and told him to add me if he wanted and he did right away. He hasnt sent me any snaps or looked at my story. It looks like he doesnt use snapchat a whole lot or facebook for that matter. So he has never asked for my number or said anything else. What the heck??? I am so mad at myself for even getting a hold of him to say drinks sounded good. What do you guys make of this? I  haven't been in a situation like this in over 18 years and I am so out of my element. A coworker who knew us both wonders if I didn't put him off with how I blew him off and was so akward about it. I could totally see that but that is why I said we should grab drinks. If he was truly interested wouldn't he message me? Look I am NOT looking for a boyfriend whatsoever but I don't get this. Is it possible he thought I would go out with him that night amd sleep with him? If so thats fine with me I would be flattered lol. I am in this whole new single world with this new body and I just do not know how to navigate it. Part of me wants to message him again and say something just to make it clear that I am interested but I don't want to because if he blows me off that will make my self esteem go waaaay down. I know it shouldn't but it would. What the heck happened and what do I do? I just really wanna go out with a cute guy once in a while and have fun. No strings no relationship. A younger guy two hours away from me that Im already semi comfortable with seems like a good place to start after my divorce and huge weight loss. 

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Be up front with him. He flirted with you when you were heavy; he flirted with you when you were thinner. As an outsider, I suspect he may be charmed by the person within. Having a limited social media footprint suggests that he prefers to live in the real world, though contacting him through FB was appropriate, and he reciprocated. Be straightforward and honest about what you're looking for to see if he's interested in what you have to offer. He may be open to being "rebound guy", or he may tell you to let him know once you get your rebound out of your system. You've known him for several years. Give him the respect and information he needs to make an informed decision on how to proceed.

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Wendy, first off thanks so much for actually reading all of that it is much appreciated! I guess I am just afraid that maybe he was never really serious about any of this and was just trying to be nice. Then again I don't really know why he would say the things he said the other day and in front of other people too? I am just still so stuck in the mindset of this morbidly obese person that nobody could possibly want me. Even though I know I look better now I still feel like I am just this old single mother who is closer to forty than thirty and who has a mess of a body under these clothes. 

I just don't want to feel like I am throwing myself at the first person who hits on me. To be honest it pisses me off that nobody else is. I shouldn't say that a 19 year old at work is very flirty what is with that lol? I get told how great I look all the time but I don't get asked out. Then again I am always just at work or with my kids so I don't know when I would? 

So if I do contact him again what the heck do I say?? I am truly at a loss as to what to say or do. I feel like if he wanted to talk to me he would have asked for my number on fb but he didn't. I do not wanna put myself out there and look stupid. I guess I better get used to that though if I'm gonna date. 

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I would just start a flirty conversation with him :) ...or the silly selfie Snapchat just for him. No need to talk about feelings or clarifying anything. Just go with the flow. Even if he isn't serious, it's so much fun just flirting back and forth. After a little bit of flirting, you'll eventually learn to read if he means it or not...but for sure, stop turning down his drinks! When it comes to the phone number thing...in today's world, if you're already Facebook friends then you already have a way to communicate, no need for phone numbers. Hope you get that Piña Colada!

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Flirting is enough for me. After I left and thought about it I was so bummed. I am just craving some flirting and fun big time. I have been through so much this past year and never have any time or anything for myself. It would he a welcome distraction. 

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You guys really don't think it would be dumb of me to say anything more since he hasn't? 

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It sounds like he's tested the water with you quite a few times and probably thinks you're not interested. You need to flirt a little and send some signals that you're interested because he probably thinks you're not since you've shot him down so many times. I say send him a flirty message (or text or whatever). Try to open the lines of communication a little more. At the very least, it'll be a chance to practice your flirting skills.

Edited by athenarose

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Those that have never failed, never tried to succeed.  That's what I say. 

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Aww thanks guys!!! 

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9 hours ago, athenarose said:

It sounds like he's tested the water with you quite a few times and probably thinks you're not interested. You need to flirt a little and send some signals that you're interested because he probably thinks you're not since you've shot him down so many times. I say send him a flirty message (or text or whatever). Try to open the lines of communication a little more. At the very least, it'll be a chance to practice your flirting skills.

This.

He might be a little confused right now, since you shot him down repeatedly and then all of a sudden opened up a little. I would venture to guess he's being guarded, that he's probably trying to tell himself not to get excited that you want to hang out because you probably just see it as a friend thing after you've rejected his advances.  

And hey, someone's got to be the rebound guy at some point. ;)  When it's the right match, it won't matter if they were the first or the 30th after the divorce.  

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I say to flirt with him a bit and nothing ventured nothing gained.  I think, like the other poster said above, he might be suddenly confused. He has flirted with you forever and you have brushed him off and then suddenly you contacted him.  Just be yourself.  He seems to really like you for you.  And now that you guys don't actually work together then what's the harm.  Flirt, go out for a drink, have fun at the wedding, hook up.  Whatever you feel comfortable with.  And like said above - it doesn't matter if he's the rebound guy or the 30th guy after the divorce.  You never know what is going to happen.  Have fun and live life to the fullest!!!

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Well I've been trying today and it seems like I get something flirty then maybe not. So confusing when you haven't done this stuff for a million years. I want him to know for sure I'm interested but I don't wanna sound like a psycho. Oh well I guess it's all practice

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You could do something really novel and message him with "You know, I'm interested in flirting with you, but I'm really out of practice; let me know if anything I say makes me seem psychotic."

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Wendy I actually kinda like that idea lol. The last I heard from him today was a shapchat and it didn't quite make sense. So I sent a snap back that said "Good thing you're cute because you don't make sense." His reply was "lol Why make it easy?"  So I'm sitting here thinking ?????? But my friends are saying that's flirting so good grief what do I know. I didn't respond back to that one. I don't want to not respond but I don't always want to be the last one to respond either if that makes sense. I told my friend I just wanted an easy sure thing and this isn't quite turning out to be it lol. They think he's trying to play hard to get now but I think he probably just really doesn't like me even though part of me knows that doesn't make sense. 

I find it sad that I automatically have to think something is wrong with him or that he couldn't possibly be serious with any of this because how could this hot young guy be interested in me?? Like because he flirted with me when I was big I can't wrap my head around that. So he must be crazy or just full of crap then? 

So hard after being married for all these years AND being fat. I just feel like I have no real idea of where I stand in this type of thing. Like what if there is no way he is serious and I look like a complete joke and nutjob? Then I remember the things he's always said and the way he acted and that doesn't make sense. Sorry for babbling guys its just that this is something that is so hard for people in my life to understand. I'm told how great I look and blah blah and sometimes I see it for a minute. But to the point that a hot twenty something is interested? Oh well the worst that can happen is he isn't and we both move on I guess. I just feel like I'm in a brand new world with a new body and self and I don't know any of the rules or how any of it works. At least I'm taking baby steps right?

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Ugh. I am stressing out on your behalf!! I am following your adventure but honestly have no useful advice for you. I'm way too much of an old married broad to figure this guy out. 

I think maybe you should just send him a message that says "dude, I'm sorry I spurned you but I was unsure and now I'm getting mixed signals from you, what's up?"

maybe you were a safe flirt for him because you didn't flirt back. Maybe he isn't sure how to go forward since you are now receptive?

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Clickin lol I love what you said. I still have the old married broad mentality! I just really do not know what to do at this point. Honestly I think I will try to hold off for a while and see if he ever gets a hold of me. If not I think that says it all. If he really was interested surely he would let me know right? If he was closer to my age I don't know if I'd be quite as petrified of looking like a moron as I am. I REALLY don't want this young guy thinking I am some crazy desperate old fat lady. I feel like I flirted and if he doesn't continue it then that tells me what I need to know. I mean how much should I say or put out there after he flirted with me in the first place?? Ugh I am just old and disappointed. I really wanted to have fun with someone I was already a little comfortable with. It makes me feel old and fat and ugly amd more unsure of myself than I already was. 

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1 minute ago, Pengworm said:

Clickin lol I love what you said. I still have the old married broad mentality! I just really do not know what to do at this point. Honestly I think I will try to hold off for a while and see if he ever gets a hold of me. If not I think that says it all. If he really was interested surely he would let me know right? If he was closer to my age I don't know if I'd be quite as petrified of looking like a moron as I am. I REALLY don't want this young guy thinking I am some crazy desperate old fat lady. I feel like I flirted and if he doesn't continue it then that tells me what I need to know. I mean how much should I say or put out there after he flirted with me in the first place?? Ugh I am just old and disappointed. I really wanted to have fun with someone I was already a little comfortable with. It makes me feel old and fat and ugly amd more unsure of myself than I already was. 

But he has let you know that he's interested. Repeatedly. And you shot him down. So, in his defense, I could see where he might think he's in the friend zone with you. But if he's replying to your messages fairly quickly, I'd bet he's still interested. His response sounds like he's flirting back. I say approach it from the mindset that flirting is harmless fun.  But that said, it's a lot easier to flirt in person than in messages. Especially when you're out of practice. You can always give it some time between messaging him. Just be extra friendly the next time you see him. And in the meantime, go find some other guys to flirt with. The more you do it, the easier it gets. Plus, if you're talking with a couple guys, it'll help keep you from getting too worried about what anyone thinks.

Also, you're not old or fat. And I bet you're not ugly either. Stop talking about yourself like that. Self confidence is one of the most attractive qualities anyone can have and a lot of guys like self assured women who aren't afraid to let them know they're interested. And that's coming from another "old married broad". :)

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4 minutes ago, athenarose said:

Also, you're not old or fat. And I bet you're not ugly either. Stop talking about yourself like that. Self confidence is one of the most attractive qualities anyone can have and a lot of guys like self assured women who aren't afraid to let them know they're interested. And that's coming from another "old married broad". :)

Yes yes yes. All of that ^^^

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Thanks guys . I have days where I think I'm pretty damn hot but others where I feel like an old mess that nobody will ever want. I don't really think I'm actually ugly but it is really bothering me that I'm not getting hit on. I'm only ever at work or with my kids though so I don't know when it would ever happen. I think it was just a rush thinking that this could easily be thw first guy I do anything with after all these years. It was quite a nice ego boost and now I just feel sort of defeated if that makes sense. I don't mean to sound so whiney. I just found out that my husband truly was cheating on me for years and it is really weighing heavily on me. This hot young guy was just what I thought I wanted as a fun distraction and a way to remind myself I was desirable. Sometimes it gets hard to believe that with being a single mom pushing forty with this mess of a body. I am still just trying to find myself. 

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The more you flirt with others the easier it will become.  Join some on-line dating sites and have some fun.  You can flirt with them before you even meet in person - if you ever do.  I can tell you that they were confidence builders for me because I had never been flirted with before because I was always heavy and had been married for a long time.  I was coming off of an extremely bad divorce and its what I needed.

And I agree about the young dude.  He had flirted with you for so long and you never responded. He probably started feeling safe flirting with you.  Now you have started respond and he may be just as nervous as you. Don't stop, but give him some time too.

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Sweet P you really do recommend dating sites? I go on and then chicken out. I cannot think of what to put on my profile for one thing. Another is I don't want to run into a bunch of people from around my little area. My soon to be ex is lieutenant at our county sheriff's department so his cheating adventures with women he is in charge of have been quite the gossip around here. I know that I did nothing wrong and have nothing to hide but the thought of people around here seeing me online just bugs me. I am so very frustrated at this point. I am craving time to get out and meet people but I just don't have it right now. My life long best friend is also divorcing and lives four hrs away. We can't afford to meet up and do anything. My other close friend is laid up from a car accident with a broken neck and several other broken bones. My third close friend is my boss and we have to be very careful where we hang out because we aren't allowed any contact outside of work. So we only go places out of town with my kids or shop in a town over and grab lunch, stuff like that. Everyone else I work with is either married homebodies or 21 year olds begging me to go out with them. I adore the young ones I work with but not sure that a 37 year old Mom should be hanginng out with that age group. Hell that is if I can even get a moment to myself to do anything. My ex watches the kids while I work and very rarely takes them overnights. Ugh I just have to find a way to get myself out there. I just get the heebie jeebies from the online thing and I don't know why. Sweet P your endorsement is making me think twice though because it sounds like you were in such a similar situation as me. 

As for young buck we still haven't had any contact since what I spoke of the other night. I have a sinking feeling he isn't going to reach out and I hate it. I might try again in about a week but I still don't know if that makes me seem desperate. Gosh everyone I'm rambling so much I'm annoying myself here. Thank you all so much for the ear and the advice. It means so much. 

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Pengworm, when I split up with my ex-husband, I made the deliberate choice not to date for a year, and I stuck to it. Not dating or even making the attempt to date is also a valid choice.

P.S. It's liberating when it's a CHOICE, not a fallback position.

Edited by WendyH

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Even just two short months ago I wanted nothing to do with any of this. Just in the last few weeks I have realized I want to get out there and meet people and have fun. I don't want a serious relationship but I do want something. We have been seperated for a year now and I have been over him for even longer than that. I am surprised that I want to date but I really do. 

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I totally endorse the on-line dating.  You can pick and choose who you want to be in contact with. It really helped my self-esteem when I'd get messages and I was able to practice flirting. I will warn you that some of the guys will go overboard with asking for pictures, etc. Those guys I would immediately block. That was the beauty of it. I could control what I wanted to do. I met up with some once I felt a little bit more comfortable with them (always at a Starbucks - but not the ones I that I normally went to near my house or work - and someone always knew where I was, etc. for safety). Many times it ended at that first meeting, but there were a few that progressed to a few dinner dates, which again I was able to practice my new dating skills. I made myself a promise that I would not compromise on certain things and as soon as someone hit one of those red flags I was out. I ended up meeting my husband on Plenty of Fish (free website, but I had also paid for Match.com at one point). I weeded out a lot of guys, and kissed a few frogs but I can honestly say that he is my Prince Charming. We've been together for over 3 years now and on June 27th we will be celebrating our first wedding anniversary.  I'm not saying that it is easy - but it was the best way for me to practice my non-existing flirting/dating skills.

Good luck with whatever you do!

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I never did master the art of flirting. I'm direct in my manner and have trouble deciphering flirting outside of an established relationship. I used match.com and met my husband on eHarmony. 

After the fact, my mom said she knew I was ready to get serious about finding a life partner when I would report back after one or two dates that I'd moved on, because I couldn't see a future with that person. And like SweetP said, be safe. I either let my date pick the first meeting place, or I'd find a neutral but mutually convenient location. 

For our first date, my husband pivked the location, and we met at a busy forest preserve for a walk. I arrived a few minutes early and read his license plate number to my aunt as he pulled up. We drove separately to grab a bite to eat and talk some more. 

As for that direct manner of mine, we met three weeks after his wife died, and as we wrapped up our date I told him that I really liked him and wasn't interested in being his rebound woman and that I was looking for a life partner. His response as we parted ways was "so am I". I took him at his word and continued to see him, be with him as he grieved, and really get to know him.

Tomorrow will be our 11th wedding anniversary.

 

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