He Brought Another Woman To Our First Date—WTF?

I met a guy through work that I’d had a crush on for a few months. One day, he came over to my desk and asked me out for coffee that night and I couldn’t believe that he felt the same way as I did. Unfortunately, I wasn’t expecting him to be such a douchebag.

  1. I put so much damn effort into looking good. I wanted him to see that I could be sassy and sexy, not the plain Jane I was in the office. I really went into overdrive to find a gorgeous little black dress and four-inch heels that flattered my body. I took care with my hair and makeup. I was ready for a hot date and potentially a relationship with this guy.
  2. I was deflated within five seconds of arriving. As I walked into the coffee shop, I took one look at the guy and my heart fell into my stilettos. My confidence just disappeared when I realized there was someone else at the table—another one of our colleagues. She was gorgeous —tall, blonde, and fit. She made all my efforts to look good for the date pale in comparison to how elegant she was in her regular life. I tried not to compare us; I just wanted to know why she was at our table sitting next to my date.
  3. The guy was as smooth as ever. I could almost forgive the guy for inviting her. He stood up to kiss me hello and he looked so gorgeous, his eyes dancing in the candlelight. Yeah, the dude was smooth, and he was throwing on the charm to gloss over the fact that he’d invited another woman to our outing.
  4. I guess I was on a three-way date then. I sat down and hoped that the other woman would leave soon. Maybe she’d just stopped by to say hi on her way to dinner with someone else or maybe she just wanted to gossip about work with us before leaving. Unfortunately not. After 10 minutes, when she still hadn’t moved, I realized this had all been planned. Why wasn’t anyone saying anything, though? It was so awkward.
  5. It was shaping up to be the worst night ever. When she excused herself to go to the bathroom, I secretly hoped she’d escape out the bathroom window, but that was silly. She was too damn comfortable sitting at the table with us. She and the guy were chatting so much and having a ball, I started to really wonder why the heck I’d even been invited. I was the third wheel here.
  6. I brought it up, hoping to make my discomfort clear. I took the opportunity of the guy and I being alone for five minutes to make a joke with him about the weird situation in which we found ourselves. I said, “Seems you’ve been asking all the women at the office out for coffee” and I threw in a light elbow tap and a huge grin to show him I was just joking. He laughed and said, “I was actually hoping to talk to you about an opportunity.”
  7. Great, now what? Was he about to talk about work? That would’ve been easier to deal with. To my absolute horror, he said he absolutely loved spending time with both of us. He was wondering if I’d be into having a threesome with him and the other woman. Apparently he’d already asked her and she was down for it.
  8. Uh, WTF? Basically, he’d invited me out to coffee with the two of them so that we could all go back to his place and have sex? Was he serious? For starters, even if I was interested in a threesome with them, which I totally wasn’t, they’d pretty much been ignoring me the entire evening. Sex with both of them would be such a turn-off for me.
  9. I laughed even though I was cringing inside. I politely told him that I wasn’t interested in threesomes and that I had to go because I had an early start the next morning. He acted hurt but I knew he didn’t really care. He’d easily find someone else to join them. What really pissed me off was that I’d really thought his invite had been a date for the two of us. I felt so stupid! Had I been wrong or was he just a total jerk?
  10. It’s sometimes really hard to read guys. When I think back to the guy’s behavior, it seemed like he was asking me out on a date. He didn’t mention the other woman or his idea of a threesome. I guess he’d hoped we could discuss that in private. But had there been other signs that he liked me? It was hard to tell because he was quite a charmer with everyone. I just don’t get it. In future, am I supposed to ask the guy if the outing’s a date or do I just go with the flow and risk these awkward situations again? Ugh. These situations can really put me off dating. It’s a minefield out there.
Giulia Simolo is a writer from Johannesburg, South Africa with a degree in English Language and Literature. She has been working as a journalist for more than a decade, writing for sites including AskMen, Native Interiors, and Live Eco. You can find out more about her on Facebook and LinkedIn, or follow her on Twitter @GiuliaSimolo.