It’s a Lose-Lose Sort of Story

In honor of Valentine’s Week and my reluctance to settle down, I’m going to share with you what I hope will make you laugh, think and most importantly, judge me.

In my last post I admitted that I go on a lot of dates. It’s true. I’ve been out with men ranging from a ripe 18 to a mature 38. I’ve been wined and dined at high end restaurants, asked if McDonald’s is OK (it’s NEVER OK), taken to strange places in the dark (no, not a park after 11 p.m., I’m not THAT gay), and I’ve even been told that one day I’ll find a man worthy of my time. I’m not sure if that last guy remembered he was on a date with me. I’ve gone on and off line to find true solace, and I’ve discussed in the past the benefits and disappointments of both venues. Like any single gay guy in his early twenties, I’ve seen a plethora of naked men (some I wish I hadn’t seen), slept in beds fit for a king and beds, well, not so fit for anybody, and I’ve certainly had my fair share of awkward (and triumphant) walk-of-shames.

But never in my almost 23 years of existence have I experienced a stalking, psychotic ex on a first date. I know first dates are supposed to be socially challenging, but a whole new level of awkward is reached when the guy’s ex suddenly starts texting and following your phone.

“Enjoying yourself?” he asks. Oh sure, but I don’t think your ex sitting out in his car is.

I don’t typically share stories from my own life on here – rather a collective sort of banter that we can all laugh about– but shit just got personal, and it’s only going to get more … delicate from here on out.

I should have cancelled our date from the middle of our first conversation. He shared with me from the get-go that he’s in school and not really sure what to study. That would be OK if he hadn’t been there already for two years. But he showed me his abs, and all logic left the room for the rest of our conversational experience. You know how that goes.

I then found his Facebook page, which I told myself not to do before getting to know him a little better, and for good reason – I stood mortified by what I saw. Now don’t take this the wrong way; I don’t care if you’re a gamer in your spare time … we all have skeletons in our closet. BUT the boy’s cover photo was Pokémon themed, and his profile picture was some sort of avatar-like-demon-thing. Man Child Alert!  I immediately thought why the hell isn’t he showing off those incredible abs in his picture or, for a more modest approach, that beautiful smile? Then I let logic come back to me and I thought, dear God I have to get out of this … right after I touch his abs. Hey, I’m only human!

I learned next that he doesn’t have a car, and he’s living with his parents. (Of course he is Matt; he’s only 20!) So I suggested what any respectful person would—a ride to and from our first date. Already dressed in professional clothing, I figured I’d make a good first impression, because it doesn’t matter what fool I’m taking out, I will ALWAYS look my best. He obviously didn’t share the same values as he approached my car in a t-shirt, zip-up hoodie and skinny jeans. To make things worse, he reeked of cigarette smoke, had bleach-blonde hair and ordered a lot of fried foods. I sat across from him eating my chicken salad and feeling like an old pedophile. I thought, is this guy 20 or 12?



I had obviously reached a very low point in my dating life.


What made me stay in my seat and not request a to-go box (I will never leave good food uneaten!) was the fact that he actually had the ability to hold decent conversation. I was shocked. First, he laughed at my jokes, and like any aspiring comedy writer, that made my insecure and selfish soul so happy. And he actually made me laugh too. Plus, I just kept thinking about that half-naked picture he sent me, and whether I could bring myself to getting him half-naked in person on the first date. Like I said, low point.

So as things were looking on the up-and-up, he suddenly stopped talking in mid-sentence and had a terrified look on his face. I thought, oh no, did he catch my over-stayed glance to his pectoral region? It’s not as bad as a straight man staring at a woman’s breasts, but it’s still pretty trashy. But no, that wasn’t it at all, and by the time all was said and done, I would have been lucky if that was the only reason he seemed distraught.

I asked if everything was OK, and he said, “I honestly don’t wanna talk about it. It’s my ex, and he’s pissing me off.” Now being the relationship and dating life writer that I am, how am I supposed to NOT talk about this? My mind was now preparing for this blog post before I knew it would really be worth sharing. But folks, it didn’t matter if we did or didn’t talk about it, because his ex certainly had every intention of making his technological presence known. Damn smart phones!

So after telling me that his ex has the capability to follow the GPS on his phone and know exactly where he is at all times, he proceeded to say that I shouldn’t worry about it because he’d only hurt him, not me. Well I was glad he spared me the black eye, but it looked like beyond this guy’s initial winning factors, he’s also a battered wife … SUCH a steal.

I just looked at him with the most judgmental eye I could muster and said, “I’m sorry, what?” (I know; I’m so insensitive sometimes!)

He then tried to assure me it was no big deal, and that the ex wouldn’t do anything ridiculous, except for maybe try to kill himself or this guy sitting in front of me. No big deal, right? I was feeling a mixture of peachy writer’s excitement and a fear that is only known by the shriveling of one’s penis, and the worst part is that I didn’t know which feeling was stronger. So I did what I do best and formulated an exit strategy. I’d get this guy home and return safely to my sweat pants and my leftovers. But the fun didn’t stop there –that would have been too easy.

While his ex was probably chilling in his car in the parking lot, I asked for the check and my date offered to pay the bill. Of course you’re going to pay the bill. That’s the least you can do for endangering my life, bucko! As he was placing the cash on the check, I get a thoughtfully prepared text message from an unknown number that says, “You enjoying my boyfriend?”


Stop the bus and take out the trash! How the hell did this guy get MY phone number?


First, no I’m not enjoying his beautiful body because YOU showed up, and secondly I’m not one to take this bullshit that your spineless ex (or maybe current) boyfriend is willing to endure. I simply told my date that if his ex continued to text me or use my number for his recreational purposes, I’d go to people who can take care of it. How’s THAT for a mob-like retort that one can only learn from the movies?

My date looked authentically mortified, and a small piece of me felt bad for him but, more importantly, the situation snapped me out of horny lustville, which we all know is the worst slippery slope to get caught in. As I drove him home, he asked that I drop him off a block away from his house because Mr. PsychoStalkerEx would be waiting for him. He assured me that his ex wouldn’t hurt him, to which I only half-believed. I asked if he wanted me to call anyone or say anything, and he said no because his ex does this all the time and only goes home crying … at least the gays don’t get violent right away.

He then, as if the night couldn’t get any worse, asked for my advice. If you know me, you know I can be blunt, so of course I had no intention of holding back. I told him I had no advice other than to seek help or grow a backbone and get rid of him. I said I wouldn’t find myself in this situation because the moment someone starts pathetically stalking me, I’d get rid of him immediately. And for the first time in all my first date experiences, I told a guy via face-to-face communication that I no longer wanted to talk, see or text with him. In this digital age when it’s easy to just stop talking to somebody via text (and they get the hint) or tell them by text or phone call that it’s not working, you know how hard it is to say these words to somebody’s face. It’s a lost art that I channeled immediately, and he simply said “I respect that … well, have a good life?” As I watched him exit my car and walk back to his house through a narrow parking lot, then through a patch of shrub and brush, I thought Yes, Mr. FirstDateCastastrophe, I will have a good life. I can only thank you for another anecdote to add to my repertoire of dating stories for the grandchildren.

Take my advice people, and when getting to know somebody (either on or offline, via text, face-to-face or through any other avenue of communication), add this very simple question to the top 10 they must answer for your approval: Do you have a psycho-stalker ex who might show up at any point during our dating experience, and if so, is having sex with you still out of the question?

Now excuse me while I take a long and hard drink for Valentine’s Day.


Written By
More from Sylvia Clark
New Year’s Resolution: Drop The Bullsh!t
It goes a little something like this: You think you need sex,...
Read More
2 replies on “It’s a Lose-Lose Sort of Story”