Badly need HELP: How do I keep him interested and convert from non-serious to serious?

DISCLAIMER: I came to this sub to seek your advice, support and understanding. Please dont judge. This is a developing story so if your advise works, ill keep you posted on what happens next if youre interested. Sorry if this is way too long.

INTRODUCTION I’m new to this sub and I’ve been learning more about RPW dating. About me and my dating history (or lack thereof): I’m a 28 year old female who had just gotten out of a 12 year serious long distance relationship (broke it off when I found out he has a live in partner of 24 yrs). My ex is 20 years older.I find that I’m more attracted to men who are smart and are much older than me.  I’ve never really experienced dating before as that was the only relationship I’ve ever had. Of course, I was heartbroken as this was the only guy I’ve ever really known and am used to my entire life.

I live a busy life mostly spending long hours at work and with family. Now that I’m newly single (9 months and counting), I wanted to experience what it feels like to date, be outging, meet new people and eventually land into a serious and committed relationship. As I venture into the dating world, I realized that it can be daunting, exhausting and frustrating. I scroll,swipe pictures here and there, read bios and find things interesting about the men, some casual chat messages and a few phone calls which really lead to nothing (didn’t meet anyone). I thought that these dating sites/apps don’t work for me as most of the guys are not really honest about their intentions. To weed out the men who are just looking to play, I decided to join this dating service where you come to seek arrangement based on what works for both parties. This I thought, could give me a higher chance at landing a more honest man who will be clear about his boundaries, desires and intentions. With the experience I had from previous dating sites, I came to the new one with lower expectations that I’ll find anyone interesting.

Fast forward to a week, I finally felt like I found a connection. Guy in his mid 40s, divorced with 2 boys (19 & 15) a  sr executive in this big company. We corresponded and finally had our first phone call. In his profile hes only looking for fun and something discreet. He was upfront about what he wanted. Hes not looking for a 1 night stand either but he finds that  the women hes dated were too clingy and were revolving their lives around him. He didnt like that. He was clear about having his own space and that he would cancel any plans or date if it meant he had to be there for his kids or something important at work came up. The women would be ok with it at first but would resent him for it later on and then leave.  He talked about his previous marriage and why it didnt work out. He said that his priorities are his kids and that his ex wife and him had made a pack to be discreet about who they will date to protect them. And that when the kids are mature enough to understand and have finished school, then both will be open about introducing new partners to the them. I completely understood this and I couldnt agree more. I listened to him and asked a few follow up questions. He was also honest about his feelings and vulnerability. That hes a man who has needs and also feels lonely and longs for someone to hold at night etc but right now not looking for anything serious.

Now, maybe this is a flaw of mine but him being straightforward about what he wants, his situation and his vulnerability made me feel connected.  It felt like it was a challenge. I have this urge to prove Im different from the previous women. I assured him that I get where hes coming from and that Im on the site to look for fun and excitement as well since Im newly single. I also talked about my previous relationship. I had a few naughty convos with him for the first week and 1 steamy hot  video call which only happened once. I realized that the guy isnt a big texter and caller and Im the type who would send gmorning/evening texts which he barely responds to. Id start a convo to get him to text me more, he would reply sometimes and would get it going then leaves me hanging and stops responding later on. This gets me frustrated but I keep it cool.

THE BUILD UP..  Three months into us talking, we agreed to meet and go over for coffee a week after.The build up was giving me extreme excitement. On the week we were supposed to meet, he stopped responding and texting. I could stil see him online but he doesnt read my messages nor answer my calls. I was worried and kept sending concerned messages. I kept my cool and was cautious about the words I used to not sound frustrated. I asked for closure and expressed that Id appreciate if he could tell me upfront that he didnt want to be bothered me anymore and Ill respect his wished instead of going silent. Still there was no sign of life from him. A week later, he texted and apologized for going ghost. He explained that he went over our convo and felt (assumed) that I was looking for something serious and he didnt want to misrepresent himself to me. He didnt want to be in a situation he cant handle since he has insinuated many times that hes not looking for something serious. He added that hes a very busy person and cant even probably do justice to a platonic relationship. So I tell him, if hes really that busy, how does he have time to pay for a dating membership and be even on the site. He said he joined the site 2 yrs ago but never really pursued anyone coz he didnt find a connection. Hes only accessed it again 2 weeks prior when he was at the airport but doesnt have subscription anymore. I apologized and has said that I didnt mean to make it seem like I was seeking for something more. I assured that I understand his concern. I shared that I thought he had gotten a cold feet since ill be the first woman hell meet from the internet. I kept my cool but at the same time asserted that he should give us a chance to meet over for coffee as theres no harm in having a friendly chat. After this incident, Ive learned to set my boundaries and not seem too clingy. I stopped texting daily but would make sure to check in from time to time. I mirrored the same effort he was putting towards. Two weeks after, I brought up the subject of meeting for coffee again, so we set it up on the eve after work. I felt confident it was bound to happen this time. Evening came and received a text 3 hours before scheduled that he has to cancel because something came up at work and cant leave early. I empathized and offered to wait but he insisted it will be too late if it were to happen as we both had to work the next day. I kept my cool and said it was ok and we can reschedule for next time. My heart sank and was frustrated. I felt like crying as I had arranged for that day to happen. Excitement dropped, any bit of hope left was gone. Just when you thought I had given up, I didnt. The more he acts evasive the more I want him. I dont understand this about myself either, I seem to like guys who are this type. I let it slide this time, waiting for a perfect timing. We still text here and there but not much effort. A month after, December came and I made a bold move to ask to see him again before the end of the year. I expressed in jest that weve been talking for 4 months, that should be long enough to convince him Im not a serial killer. I let him know that Im not the type to easily give up but if the meet doesnt happen this year, I doubt it will ever happen. I assured that I have no expectations and that I just wanted to meet him because I like and find him attractive. Of course I was cautious with how I used my words as I didnt want it to sound like Im giving an ultimatum. At the back of my mind, I was already losing hope and interest. He replied and agreed again to meet for the 3rd time. I was already skeptical but I gave it a shot. I grew more anxious as I anticipate the days leading to our meet up, I wasnt as excited because of the previous incidents.

FIRST MEETING.. Judgement day came (Day after xmas). I arrived 30 mins early and texted him of my whereabouts. He came on time. I got in his vehicle and said our greetings and pleasantries. He didnt seem nervous but I can sense a little shyness at first. I wasnt nervous at all, we were in the vehicle for about 30mins as he was driving to our destination (Starbucks). I asked if its ok for him to hold hands as we walked to the coffee shop and he was cool with it. We Went over for coffee and had a fun and serious conversation basically about each others career, romantic and personal life.  We got back in the vehicle and was parked for 30 mins waiting for my driver to pick me up. I had this assumption that our first meet would be sexually motivated given we met at that site and had done a few naughty stuff prior but turns out he was actually respectful and behaved.  I was wearing a V neck dress (cleavage showing) and stilletoes. He made a  comment about my outfit, asked if I was wearing a bra. So I answered yes and grabbed his hand put it under my bra so he could get a feel. I teased and said, see I told you Im wearing one. He played with my breasts without hesitation. I asked if he could suck and bite them, he obliged and suck them gently. He didnt bite coz he was concerned it might hurt me. People were passing by us so he had to stop what he was doing as we run the risk of getting seen from the inside of the vehicle.  There was a bit of silence so I asked if its ok to get a kiss, he said yes. I leaned over to kiss him. A smack and a little nibble on his lips. He seemed passive about the kiss, probably wasnt sure what kind of kiss he was getting. You could hear a pin drop from the silence. I did this again and he was still passive , no tonguing though, just me nibbling on his upper and lower lips. For him to return the gesture, I asked if he could kiss me back and he did but was only a kiss on the cheek. I smiled and asked why only a kiss on the cheeks, he replied that there are cameras in the area and where we were parked had a bunch of lights directed towards us (the windshield), people outside could see us.He talked about how he has access to the cameras and can zoom in out, at his job and could hear peoples conversation if he wanted to but would never dare do it if it didnt require for his job to do so. It was getting late so both of us were tired, we held each others hands. As the clock ticks, he made a bold move to put his hand under my dress and started to carress  my thighs.I was getting wet, a bit conscious and shy at this point...when my driver arrived (thank god) lol. I had to leave and we kissed each other goodbye with a promise to see each other again after the holidays. An hour later, we update each other of our whereabouts, he said he had a great time and looks forward to the next meet (he doesnt call it a date but a meet) with a blushing emoji. That evening, I didnt realize that I had forgotten a gift I had bought for my boss, in his backseat. He promised to give it once we meet again.

THE AFTERMATH + SECOND MEETING.... Having met him, I expected that maybe this time he would text or reply/communicate more. I guess there was change but only at a bare minimum. January came we both were busy with our careers. I kept my distance and would only return the effort hes giving. 2 weeks before Feb I expressed my interest in seeing him for the 2nd time, probably by Feb 13 or 14 + I needed to get the item I had forgotten in his vehicle so I can gift it to my boss. He gave assurance that hell take note of it but 14th maybe a no as its a valentine day where people are out and about causing traffic on the road. I pretended that I was oblivious to the fact that 14th was a Vday.  I looked forward and waited patiently. That week came, we agreed to meet on the 13th. I planned out my schedule and made sure to look damn good even though I was a little anxious. 2 hours before scheduled I notify that Im leaving work in a few to our rendezvous. 10 mins later I get a text that he has to cancel as he cant leave work early due to an urgent matter he has to address. Its hard for me to believe this now as its becoming a theme already. I was extremely upset and frustrated but I replied with understanding and assured that I can wait and will be at the rendezvous on time. He insisted he cant make it and has an early meeting the next day. I expressed a little disappointment by saying he couldve told me at a much earlier time so I didnt have to leave work early, I cant go back since Im already on the road. I politely insisted that he doesnt have to stay long and just hand me the item so I can give it to my boss. He apologized and said that hes not the type of person who just cancels unless its a valid reason. He offered to have the item shipped the next day if it was really that urgent. I went quiet for 5mins thinking of a good reply. I responded that the item is indeed important but I also wanted to see him. He replied and offered to swing by the next day (evening) Feb 14 for a few minutes. I didnt respond and got to the rendezvous and notified him. He replied and said he cant make it. I assured that I understand and that I just felt the need to let him know and I was going to leave after I pee, with or without him. That night was horrible I felt like I was yet again rejected and dismissed. So I went on another date with a friend instead. Yes Im not putting all my eggs in one basket.

The next day, I let him know that I needed him to confirm by 6pm if the meeting is on or not. So I let him know Im already at the meeting place and hes on the way. I didnt know what was bound to happen that night since we didnt have anything planned. While I was waiting he texted and asked politely if its ok to get him a drink at SB since I was already there waiting and that hell pay me in the car, hes too tired to go outside. I gracefully said its fine and he didnt need to pay me since he paid for the drinks last time. He arrived, told me where he was parked so I went. I was a little anxious but kept my cool. Got in his car, smiled, handed him the drink and he said thank you. He handed me the item I had left in his car and I apologized for the inconvenience and thanked him for still seeing me despite his busy schedule. He may have sensed that I was upset from last night which is why he kept his distance and there was little silence for a while as we sip our own drinks. I jested and asked why I didnt get a kiss, he gave me the same reply last time, lights directed towards us and didnt want people passing by to suspect that we were doing something. I let him know that I understand then asked how much longer he can stay, said he has 30 minutes. I didnt want to bring up what happened the night before so I just looked at him and gave assurance that I wasnt mad and that Im happy he made it tonight (Friday).(He picks up the kids every Friday to stay with him during the weekends. So him making time for me on a Friday is a big deal to me since I knew the weekend is dedicated to the kids). He replied with, oh yeah Thanks. We talked for a few more minutes as we finish our drink. I told him about the problem I had at work which almost cost me to lose my job and I almost didnt know what to do. He asked what happened so I told him. He commented that I couldve come to him sooner so he couldve helped me out with how to work around it as hes been running companies for yrs and yrs and knew the due process etc. In this meeting, there was no petting or anything, I didnt ask to hold hands, I didnt attempt to seduce or do anything since he already set the tone when I arrived (not giving me a kiss coz hes concerned people could see us from the outside). I let out a cute sigh and mumbled that maybe there wont be a 3rd meeting, he reacted and made a promise that well see each other again when he gets back from out of the country for a week. Its just that hes busy right now due to a lot of movements at work (higher boss will retire end of Feb and hes next in line to take the post). Hearing this from him gave me a little hope that there will be a 3rd meeting. Time was up and we had to go. Thanked him for the time and asked for a kiss. He obliged and had his lips pouted ready to kiss me. It was a quick smack, then I went for another one..then off we left. We both update each other as soon as we arrive home and said our goodnight.

OBSERVATIONS From what Ive observed, hes careful with his words, weve had conversations but Ive never heard him say the words "love, date, fell in love, i miss etc". First week we started talking, he only asked about how Im doing 2x. Up to present, I mostly am the first one to text and ask how hes doing but like I said, I stopped over texting and only check in from time to time (maybe 2 to 3 txt per week). Hes only addressed me by my name 2x and this was in text when we first started talking. But to be fair, we havent disclosed each others complete name..yet, we only go by our nickname. Hes not complimented me yet. Id like to think that he doesnt do so coz he didnt want me to misinterpret his compliments since he is not into something serious. He has shared pics of his kids though. I dont know where he works nor does he know mine. I tried to ask his position at his job but wont share so I didnt insist coz Im tryjng to respect his boundary. So yeah theres mystery in all this. Id like to think he really is who he says he is (divorced and not cheating on his wife). I have asked if he has a live in partner and he strongly replied with no, if he did he wouldnt be out on a Vday. No other observations or red xflag other than when he cancels our meet up.

THE PLAN: HOW DO I KEEP HIM INTERESTED? I appreciate if you got to this part of my post. Please dont judge me. Im not looking to rush into things with him. I know hes not serious right now but Im hoping that over time, Ill be able to earn his trust and affection. Somehow, I have this theory that maybe hes giving me a test? Is he testing my patience and how committed and determined I am? Maybe hes purposely cancelling in the hopes that Ill go away sooner or later? I dont know. I want to show him Im different than the rest of the women hes met.

Im running out of ideas on what to do when we meet for the 3rd time. I want to keep him interested and actually spend quality time with him every time we meet. I have asked for his input on what he wanted to do from the last 2 meetings we had but he doesnt give any input and he seems to let me drive the situation.  

I do my best to be as feminine as I can be. Compliment him, listen to him and show appreciation and be sexy for him. I dont want to seem aggressive and masculine as this might put him off so I try my best to be gentle and staying true to myself.

Can you please give me ideas on how to keep him interested and motivated?  What should I do on our 3rd meeting? We plan to meet next week Thurs/Friday.

How do I convert him from non-serious to serious? Im not rushing things, Im giving myself 1yr to be able to convert him or at least keep him interested. Its been 6months and running since we started talking. 

I have this idea for the next time we meet, where Ill express how Id like for this to move forward. I.e how often we can arrange to meet/spend time (1or2x/month), things we could do together, how often he should try to communicate/respond to texts, and maybe request for him to ring me sometimes since he doesnt ring me at all, only text, so I can hear his voice. Is this a good idea?If so, how do I go about it? Is the 3rd meet the right time to talk about this or do I wait 2 more meetings to do so? I want to use sex to keep him interested but I am not all for it as Im afraid hell ghost me right after. What am I doing wrong? What am I doing right? How do I keep my frame?  I really feel a strong connection for this man. Hes so mysterious, very masculine and smart which keeps me more interested and drawn to him. Its been 6months since we started talking and I still feel strongly for him. 

Please dont tell me to dump him and find somebody else coz thats not the answer I seek.

Your help is much appreciated. Thank you ladies!