Confessions of a serial first dater

Wonder why women block, unmatch or simply fade away after a date? Welcome to the world of a woman who has done all that and more. Find out why she went on 50+ first dates and finally switched dating apps in her quest for a decent guy. Mission (im)possible?

Confessions of a  Serial First Dater ILLUSTRATIONs: Azad Mohan

Recently, Tinder informed me that I had more than 10,000 likes. But this grand total of likes doesn’t tell the whole story because I have only right swiped a fraction of those likes, and when it comes to meeting those matches, very few even made the first date, let alone round two.

But, I am jumping the gun here by discussing dates. Let me walk you through the prelude to my dating history. After 50+ first dates and counting, I used to think that I was doomed to go only on a first date. If this were a time-lapse video, at this point it would take on a Chaplinesque quality with me making faces at my phone and swiping left in rapid motion blur. Then the scene would change to a dramatic right swipe with a drumroll. The screen would pop with conversation bubbles above my head. Then it would show me in a restaurant with a guy. That’s when I’d break the fourth wall, look straight at the camera with an eye-roll. 

However, since I can’t describe the story of my serial first dates as a screenplay, I will ask you to picture it as vividly as you can. So, I ask you to imagine that you are a confident, successful, awesome, single 40+ woman. Now imagine you are ready to go on a quest and totally prepared for the swipe-a-thon, which will lead you to your heart’s desire.

Awww Snap!

No, that’s not your Wi-Fi going down. That’s you crashing back to earth from this la-la land fantasy of finding a date the moment you start swiping. You will sigh as you realise that your dream of spotting a Jason Momoa-like guy will NEVER EVER come true. Then you will lament, “All the good guys are taken.” Finally, you will give up these pipe dreams and be ready to settle on any decent guy. All you are looking for is a guy who is smart and single so you can have a good time together. That’s when you actually pay close attention to the kind of dating profiles you have seen. 

Is a decent pic too much to ask for?

One would think that men in their 40s would be able to put up a decent profile pic. After left swiping countless group pics (don’t want to guess who), motivational quotes, dick pics, porn, cross-dressers, dog pics, cat pics, travel pics, nonsense pics (the kind your ass clicks when your phone is in your pocket with the camera on), you make a pit stop when you see a real man. Then you come to terms with the disappointment of discovering that every pic is taken to hide a balding pate. Now, don’t get me wrong, I like bald men, it’s the attempted camouflage that I can’t get on board with!

Sometimes the first pic is neat and then the guy is surrounded by Vegas showgirls. Is he trying to show off? That is not something you want to boast about unless you are looking for sugar babies. Then there are the endless gym selfies. Blah.

Will a real, smart man please show up?

Then it happens... all of a sudden there is a pic that grabs your attention. But wait, nope, there is no bio to go with it. What kind of man doesn’t introduce himself? Don’t know, don’t care. Moving on to the ones who do write a bio. Swiping past the sugar daddies who “Live life king size” and the ones that bitch about all that is wrong with other people’s profiles, and the ones who want pity swipes with their “Nobody ever right swipes, wondering if this app works” sob story.

There you encounter the garden variety sapiosexuals, gym freaks, travel freaks, those looking for like-minded people, but not revealing what is on their mind. After a while, you start seeing many strange patterns emerge. Like so many guys mention their Uber rating right down to the last decimal on their bio. How is a girl to gauge a potential date based on what cabbies rate him? 

Do we all have an Uber driver alter ego that I am not aware of? Even though my Tinder ‘like’ score is more relevant to my online dating profile than an Uber rating, I don’t put it on my bio.

After wading through all those bios, you finally hit upon one that has a decent description.

Congratulations! It’s a match!

You think you are one step closer to going on a date only to discover that matching and exchanging numbers is like a dating milestone for many guys. Don’t ask me what they do after amassing all those phone numbers and never texting or calling or meeting. Then there are those who are bread-crumbing or dropping you a line every once in a while to stay in touch. I did not know WhatsApp forwards are a way of letting you know they are there and that you are a shoo-in for a date the moment a free slot is available on their calendar. Once you get past these hurdles, you move to the conversations where my confessions begin.

I won’t bore you with the saga of the endless “did you have breakfast” type lazy bums or the “Good morning gorgeous” type serial greeters. I will talk about the underbelly of the online dating world which I discovered is both entertaining and educational. Yes, educational. I had no idea what NSA, FWB, NSFW meant. I did not know about bread-crumbing or ghosting. I did discover some fetishes and sleaze, but it is totally unprintable and to know more about that you have to wait till I become a stand-up comedian.

Let me walk you through some of my dates and you can decide whether I am right, or at the very least, laugh with me. 


Let the confessions begin…

Is it going to be only coffee or something more?

When a guy asks whether I want to hook-up even before meeting me, I wonder why they don’t go to an escort who will guarantee sex after dinner. It is a constant surprise to me how these guys don’t realise that for most women sex is available on demand, and merely a text message away. So if all they can offer is sex and some crappy mind games on the side, then they may have to get in line (pun totally intended).

Seriously, if it is just sex they are after, then why seek smart, funny, confident women? Women like me are not looking for them to fill a hole in their life, both literally and figuratively.

They are seeking witty, fun to hang out with guys who can match them and make it worth their while to date.

But this is a hard won realisation. In the beginning, I just went with the flow. So when I encountered the “octopus” as most girls refer to extraordinarily touchy feely guys who are totally creepy, I was in for a surprise. No sooner did we sit for the movie, did he start trying to feel me up. His fingers inched towards my dress, it would ride up and I would push it down. Did that make you cringe?  Yeah, me too. Nothing is more unwelcome than unwelcome attention, especially in a public place. I said No multiple times and he finally got it, but obviously I didn’t care for a repeat episode.

Confession No.1: It is not like I haven’t made out on a first date, but it has been spontaneous and not part of an agenda and certainly not with someone who has set expectations about what kind of action should take place at a cinema theatre. But ye dil maange more. Wham bam? 

No thanks Sam! To borrow a phrase from Marie Kondo, the person needs to spark joy.

Married but still…

For the longest time, I had no clue why people wrote their qualifications on their bio. But when you read MBA in profile after profile, you wonder is this a business networking platform on the side. Then, someone informed me that it wasn’t a degree but an acronym for Married But Available. That made me want to put up SBU in response, which stands for Single But Unavailable. 

Then I matched with guys who were married and content to be friendzoned, which made me think that it’s not all bad to match with a married guy. I couldn’t have been more wrong. There are many men who claim to be married but single in the city they are visiting.

There was this CXO level guy who told me that he was in the midst of getting a divorce and that he definitely wanted to know me despite me telling him that I wouldn’t date him because he was not legally in the clear. He even added me on LinkedIn so I thought he was legit.

By the time we met, the plot had unravelled and how. Not only was he not in the middle of any legal proceedings, he was not even separated. When we met for dinner, he told me he was keen on a serious relationship and didn’t mind a relationship with someone (meaning moi) in the interim. He was actually surprised that I minded dating married men and tried to convince me that I shouldn’t have a problem if he didn’t. It is not as though I was seeking marriage after all.

Many married men don’t realise that just because I am not groom hunting doesn’t mean I am sitting around waiting for scraps of attention from a married guy when it suits him. He just couldn’t understand why there was nothing in it for me till I actually spelled it out for him. Here I am in all my awesome singledom. I don’t have any handicap like not being available on weekends. I am witty and funny and confident (all his words). I can go out with a person who doesn’t have to wait for his wife to turn her back to escape. I don’t have to provide a shoulder to cry on for all the wife-bitching he does. Then why would I saddle myself with a guy who is in what can only be described as a bad marriage and not even separated?

As I explained all this, I could see his face become smaller and smaller and when he vanished without a trace and not even a token bye on WhatsApp, I couldn’t help but wonder why he would think even for a moment that he had a shot with me despite knowing my stand. Why credit me with intelligence and fail to understand that I know my own mind? I have encountered many men who claim that they want to date strong, intelligent women, but have no clue how to deal with us when we see through their bullshit.

Confession No. 2: I met another  married guy who not only lied outright about being divorced but convinced me in an award-worthy performance that the reason for his divorce was impotence. It took me a second date and some Facebook sleuthing to figure out the fellow was married. I have a sneaky suspicion that the next instalment in the impotence story would have been about me magically curing him of it. Yes, there are men who are that desperate. Now, I ruthlessly unmatch not only married guys, but also the ones I suspect are lying.

Oh! You are so gorgeous and so much fun! I know. But how are you?

There is a beautiful meme which shows some of the spectacular things most males from different species do to attract a female. In contrast they show the human male who after so many years of evolution, just shows up. In fact there are some guys who even today expect you to dress up for a date when you are meeting them after work. One such guy who was totally dishevelled and even risking a shirt button popping on his belly, looked me up and down and said that he thought I would wear something exotic. I was tempted to inform him that this is not a “ladki dekhne ka programme”. But, what’s the point when I didn’t need to meet him ever again? My most awkward date was when this guy sat across the table and kept staring at me. He said I was even more beautiful than my pics and that he was just admiring my beauty. I have never been more self-conscious. And I can stand on any stage and address as many people as you can fit in a room. But I was stumped by his silence. He wasn’t creepy or disrespectful, just clueless about dating a real woman. I was his first match. It was worse than many people’s first time in bed. He would only speak in response to a direct question. I felt the need to fill all the silences with funny anecdotes and asked too many questions about his life than I cared to know.

Then there was this guy who knew we had nothing in common. His idea of a good time was to drink himself silly for which he knew I wouldn’t be good company because I am a teetotaller. He told me I was too sweet to let go and kept trying to wrangle a second date. I tried to let him down gently by pointing out that he and I were very different people. But, he wouldn’t get the hint and I had to ghost him.

Confession No.3: There was a time when all this flattery felt like appreciation. A time when I was still vulnerable like that. While I didn’t think that I was as gorgeous or as bright as the sunshine they called me, it still felt good to be complimented. But, now I don’t meet a man who feeds me lines, I need him to be as fun and as gorgeous as he thinks I am.

Time to lean in 

I decided to take Sheryl Sandberg’s advice and decided to lean in on the women in my circle to figure out how to break the first date only jinx. After all, their collective wisdom could get me to round two if nothing else. With so many disastrous first dates, my friends initially thought I was being picky, but later they all told me it wasn’t me, but the app which was at fault and that made it my phone’s fault too. I was on the one app that had a terrible rep. I had an old Moto G which did not support the latest dating apps. Men on Hinge are so much better they said. So I decided to take their advice and got myself a swanky new phone and installed a different dating app. So I am moving on to greener pastures. I hope that the sensible men have migrated to that platform as well. Fingers crossed. 

Wish me luck! 


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