What 5 Years of Online Dating Did to Me
My Evolution from Newbie to Veteran
I began online dating a little over five years ago. I hadn’t dated since the prior century, my self-confidence was low, and I had been warned about how bad online dating was.
I was scared and nervous, but threw myself into the process (with my therapist and dear friends nearby)!
The reality is that you can research, self-reflect, and prepare only so much. Eventually you have to jump in.
And one can only truly appreciate the murkiness and challenges of the online dating waters once he or she’s actually immersed.
I recently realized how differently I approach dating now vs. then.
It’s been an evolution over the past five years.
I’m a lot savvier and more confident these days.
But I’m also wary and jaded by the process.
Miraculously I’m not bitter, though!
My heart’s been beaten up in the process but I still believe in love!
Online Dating: Newbie vs. Veteran
Communication Prior to First Date
Newbie Bonnie
In those early days, I enjoyed getting to know guys before I met them.
I texted.
I initiated a fair amount.
I followed up.
I asked to talk on the phone.
It made the first date less awkward for me and allowed me to weed out the occasional mismatch.
It also meant that I put in a lot more effort on each guy and in the process in general.
I was still learning about myself, guys in my age bracket, and what dating looked like post-divorce.
At that time, I didn’t mind putting in the extra effort.
Part of that was for my own growth and information.
But, yes, a lot of that effort was for the benefit of these guys — guys who were strangers to me.
I assumed that I would most likely meet the guy for the first date, so I was motivated from that perspective as well.
But the extra emotional energy put into these “potential” relationships often left me drained and depleted.
Veteran Bonnie
I text if the guy does, but otherwise I don’t put a lot of effort in.
I rarely ask to talk on the phone anymore.
Now I know that having an amazing connection via text or phone means nothing.
I prefer locking down a potential meeting time/place sooner than I did when I first started dating.
A veteran online dater fully appreciates this cardinal rule: Chemistry can only be determined in person.
My Questions/Concerns Before a Date
Newbie Bonnie
Will he be attracted to me?
Is he just interested in sex?
If so? What kind of sex?
Will we connect?
Will our schedules be compatible (since I have a son and many of the guys I date also have kids)?
Will he show up?
Is he interested in something that could become more serious?
As I reflect on those first 2 or 3 years, I can see that I was more concerned about “him” rather than myself.
If he would be interested in me. If he would blow me off.
That I wouldn’t be good enough or wasn’t doing something right.
(Thankfully that never translated into me doing something sexually I was uncomfortable with. But it did lead to A LOT of tears and holding myself responsible for things that had very little to do with me.)
Veteran Bonnie
Will I be attracted to him?
Is he just interested in sex? If so, how quickly can I get him to be honest about what type(s)?
Is he over his prior relationship(s)?
Is he going to insult me?
Will he ask for a pic of me? (Which means there will be no date. That he will most likely call me a prude, say other cruel things, then disappear when I refuse.)
Will he try to send me an unsolicited pic?
Will he be mad that I don’t drink? (Yes, that’s happened, too. One guy ghosted me entirely. The other 2 or 3 made sure to grumble. I cancelled those dates.)
Will my car be too nice?
Will I like the wrong kind of pizza?
Will he request that I not wear undergarments?
Will we have any chemistry?
Will he blow me off all day then ask me “out” at 11:45 pm? (When he asked if he was being rude, I assured him he was being sleazy. I never heard from him again.)
Will he blow me off for an entire week then ask me out at 7:30 pm by texting me “hang tonight?” (I never responded.)
Will he insult my meeting place as being too hipster and proceed to pick the most hipster place in all of Austin to meet (with no parking on top of everything else)? (I cancelled on him, too.)
Honestly, these days I am MUCH more concerned about what, ahem, shenanigans a potential date will pull before we even meet!
In fact, most of the time I assume the date isn’t going to happen.*
That’s not me being pessimistic as much as knowing that there are so many pitfalls to a date actually happening.
It’s a nice surprise when the date actually does happen.
(*My personal experience backs this up. The men I match with have gotten much more aggressive about sex in the past 2 years. Ghosting has become even more frequent as well.
I’m not quite sure why that is. But friends and readers here on Medium have confirmed that the online dating climate has evolved over the past several years — and not for the better.
Fortunately, I’ve gotten savvier about what sexual code phrases mean. I’ve also gotten more direct about asking questions if the opportunity presents itself.
This allows me to avoid an uncomfortable first date with someone who is seeking casual sex or merely testing the online dating waters rather than looking for any sort of relationship.)
I don’t worry nearly as much about the impression I will make on him. Because I’m more comfortable with the process and who I am regarding dating.
I still give every date my best. I dress nicely. I bring my most charming self. I’m friendly and engaging. That’s my part of the bargain.
But I’m able to take the first date less personally than I did when I was a newbie.
I also go in with lower expectations than I used to.
After the First Date is Over
Newbie Bonnie
I immediately thanked my date via text for meeting me. No matter how he treated me or if we had a connection.
I was worried about him.
If I was interested in him, I was fairly enthusiastic and communicated a lot.
Veteran Bonnie
I still thank all dates within a few hours of the dates.
However, if someone doesn’t buy me anything and never texts me, I typically don’t write anything either. (Usually I’m a cheap date anyway, but if you didn’t even get me a Coke, I don’t really owe you anything.)
I’m more guarded about a first date that seemed to go well.
Guys disappear after what I deemed a good, or even great, date. Or wait until the third or fourth date to come clean about their sexual preferences (like wanting to make sex tapes or needing sex based on my degradation — I passed on both of those).
If I’m interested in someone, I try to be patient and let them initiate contact after the first date.
I’m trying to be more chill these days and give guys a chance to reach out to me first.
That hasn’t worked out very well, but I’m sticking with that approach for now.
Just a few years ago I was naive and unsure of myself regarding dating.
Over the past 5 years, I have worked hard, gone on a ton of dates, cried a lot, made missteps, learned from those mistakes, taken breaks when needed, and have gained a lot of insight.
I still make mistakes. I’m still learning. But these days I know so much more about myself, what I’m looking for, and what I’m not looking for.
Sure, I wonder if I’ll ever find someone special. It’s hard not to be discouraged after so many dead-end first dates over the years.
Still…
Even though I remain single, I’m proud of my growth and courage to put myself out there!
Bonnie was off the dating market from 1998 (when she met her now ex-husband) till early 2014. She has been online dating on-and-off for almost 5 years. She has gone out on at least 100 first dates, interacted with over 1000 guys, and reviewed at least 10000 profiles. If there was a Masters in Online Dating, Bonnie’s earned it. This means: (1) That Bonnie is a failure at dating AND (2) She’s accumulated a lot of experiences and knowledge about the dating landscape for middle-aged chicks in Austin.
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