How To Lose A Guy In 10 Minus Four Dates

Honesty is so important when dating, yet many of us are hesitant to be honest when we need to most.

We fear causing people emotional pain so we avoid saying what needs to be said, but most of the time that ends in apologies and hurting them anyway – maybe even more so than if we’d been forthcoming with them from the beginning.

I wrote a blog post several weeks ago about an experience I had going on a date with a man who lives in New York City. I went on at least five dates with him afterwards, but remained silent about them here. Mostly because I felt like a huge asshole.

I knew there was zero romantic chemistry on our first date, yet I continued to see him. I thought writing him off after one date would’ve been a mistake, even though I was pretty sure there was nothing more than a friendship there. While he made me laugh and I had a good time, there wasn’t a spark.

Even so, I wanted to give “us” a chance. I wasn’t sure if my not being attracted to him was because I was more into someone else I was beginning to develop feelings for, or if it really was because we were simply not meant to be.

Plus there was the fact that he’d impulsively bought us tickets to see Wicked 24 hours after our first date – the show was not until a few weeks later – and damn it I’d been waiting years for someone to take me to see it!

I’d never dated a man who was successful enough to throw around money before. I’d become accustomed to cheap dates at dive bars – which I actually like, by the way. Being treated to expensive dinners, drinks and gifts was so foreign to me.

As a single mom I don’t have a ton of money. Most months I struggle to pay my bills. Because of that, I don’t go out very often. Three nights out of seven are usually spent cooking myself dinner and sitting at home alone with a $5 bottle of wine. The other four are spent with my son.

While I’ve never been much into material things or going out all the time – being wooed by this guy felt amazing. He showed me a world I’d never experienced before – and that world was addicting.

When we went out, he showed me off like a trophy – I guess being 46 and dating a humorous & smokin’ 33 year old woman like myself is pretty impressive!

He made me feel like a princess.

But he was also showy and a bit pushy – which made me uncomfortable. I drank on most of our dates to take the edge off.

By date four I knew there was no chance in hell I was ever going to sleep with him, though it wasn’t just because there was no spark…

In the time between those four dates I’d also fallen for someone else.

You know, that guy who writes that blog that rhymes with bourbon hater

And while I knew things weren’t going to work out with this other person, he still had my heart.

Still, I couldn’t find the courage to be truthful. I’d come to care for Mr. Loud & Pushy as a friend and did not want to hurt his feelings.

“Just be honest with him,” a third party advised.

But being honest was going to make me the bad guy – though truthfully allowing him to spoil me knowing full well I wasn’t attracted to him had made me the bad guy already.

There was no way to tell him I wasn’t attracted to him without bruising his ego, so I played the wounded single mom card and told him that “After all I’d been through, I just wasn’t ready to be in a serious relationship yet and could only be friends with him, right now.”

I should’ve left off the right now. It was my chance to be mostly honest – but in addition to not wanting to hurt him, I just wasn’t ready to give up being treated like a princess yet.

I told you that shit was addicting.

And yes, I’m an asshole.

Not to worry – my being an asshole caught up with the next day when he called me up to ask me if I had a passport. When I said yes he told me he wanted to take me to Cancun for an all expenses paid vacation. He was with his travel agent and she’d found a deal at a fancy resort in February.

When I checked out the website, the photos of the resort literally took my breath away.

“No pressure – we’re just going to hang out and relax and have fun…” he said.

But I knew damn well that if I went away with him for four days, with us sleeping in the same hotel room, he was going to expect me to have sex with him.

I’ve always considered myself a good person. I’ve never used anyone for anything in my life, but the idea of getting to go on an all expenses paid vacation to lay on a warm sunny beach in a bikini and do shots of tequila all day – a vacation that would probably take me another ten years to pay for to go on myself – made me think about it.

Sheeeett…Another ten years is a long ass time to wait to go on a vacation when you  have one laid out before you on a silver platter.

I told him I needed 24 hours to think about it, but really I was just stalling the inevitable.

I knew I wasn’t the type of woman who could use a guy for a vacation and still look at herself in the mirror.

So 24 hours later I politely declined.

I could tell he was upset with me, though he said he understood and that “we could do it another time.”

I shuddered at the thought of “another time” and resolved to finally be honest with him the next time we were face to face.

But a friend beat me to it when he called her up to try to find out why I’d refused to go on vacation with him.

You see, he’d already paid for and booked the vacation because he was so sure I’d say yes.

Which was an idiotic move on his part – but I digress.

She became so irritated with his incessant inquiries as to why and how I could turn down a free vacation with him that she blurted out the truth – that in addition to having feelings for someone else, I was in no way, shape, or form, interested in being more than his friend.

Ya think his feelings were hurt? I’m thinking yes.

I now owe him an apology if I ever see him again.

The lesson here?

There are two:

1) I’m an amazing & good-hearted person, but I also have a bit of asshole in me. Maybe everyone does.

2) Honesty is so important when it comes to matters of the heart. When dating, tell people who you are and what you’re about without apology from the very beginning and a lot less people will get hurt and a lot less apologies will be needed.

Share Button

Related posts:

  1. Men Are Like Orgasms: Why Multiple Dates Are Better Than One
  2. Shut Your Whore Mouth, Insecurity
  3. Just Me, Again.


  1. Mark says:

    Your intentions were good. This was gonna be painful no matter what happened. The question is … peel the bandaid off slowly or rip it off quickly? And I think that depends on you, and depends on the other person. Me, personally – I prefer the bandaid ripped off quickly.
    Once his emotions settle hopefully he’ll realize that you were trying NOT to hurt him, and perhaps that hurt him more in the end.
    Sometimes life is just like that.

    1. Mely says:

      I really did have the best intentions. If I didn’t have a conscience and a heart I totally could’ve made him my “Sugar Daddy.” But it was selfish of me to string him along just because I really enjoyed having a friend to go out with. Had he not treated me to things I probably would’ve written him off way earlier.

      I think it was the timing too. I’d fallen for someone else that I couldn’t have and wanted to get over him, and I thought maybe continuing to “date” this guy would help me with that.


      Dating is hard. But I learned some valuable lessons here so I won’t make the same mistake again.

  2. Brad says:

    Well I appreciate an honest woman and so far I’ve only been disappointed with that policy a scant 20 times in the past 5 years. Two times when I was out on the first date the gal I was with said she had a wonderful time, that I was a breath of fresh air, but she wasn’t interested. All of the other times I’ve had to McGuyver it out of them – thus making me look like an idiot that ‘didn’t get it,’ or ‘can’t take a hint.’

    Lately I’ve just come out and basically said thing like, ‘I’m interested in seeing you again and spending some time together, and I’m going to keep asking despite the look on your face right now that looks like you’ve swallowed a a dung beetle. . . with the dung ball attached.’

    Over the course of human history, the male sub species has adapted perception receptors to pick up on positive female signals in close interactions – phrases like ‘not ready for this right now,’ and ‘I’ll be busy that week,’ ‘You’re dead to me assface,’ to mean ‘I want you sooo badly, just keep asking.’ So instead of asking you to the local watering hole, the more financially adept amongst our clan tosses a few incentives on top of the clumsy proposal.

    Yeah, have a nice time and tell us you’re not interested so we can get home before Sportscenter’s over.

    1. Mely says:

      The thing is, we were similar in that we both like to laugh, have fun and live life to the fullest. I thought maybe something could grow from that so I didn’t want to write him off after one date. Looks don’t mean shit to me, really. If you can make me laugh I’m halfway yours…

      Treat me well and I’m 3/4 of the way…

      But he came on really strong and started throwing material things at me so quickly – probably due to some insecurities – which complicated things since I’d never been treated like that before. I mean, what woman doesn’t want to be wooed? I couldn’t think clearly with all of the pretty things & experiences coming my way.

      By date three he’d already spent more money on me than most men I had dated for months. I thought giving three dates a chance would give me a clearer picture. And it did, but then I’d felt guilty that he’d spent so much money on me and didn’t want him to think I’d used him.

      Plus I really did come to care for him as a friend.

      I feel super shitty, though in all honesty I think even if I had said I wasn’t interested on the first date he still would’ve kept trying to woo me.

      Life is weird.

      Maybe I should spend more time in my underwear watching Sportcenter…

      1. Brad says:

        We’ve all been there Mely. Of course I don’t know everything about the situation, but some guys think they can buy their way in – which can be in some cases an effective mask for some really shitty things. Who doesn’t want to hang with someone who doesn’t have to hustle to pay the bills? But that doesn’t buy honesty, a sense of humor etc and it certainly doesn’t by attraction. It’s a typical male ploy – ‘I got you this, now you gimme that.’

        Listen, if he’s opening the wallet to try to woo you, he’s also got to take the responsibility on himself that it might not work, unless he’s an arrogant tool. I know it’s easy to say, but don’t beat yourself up about it. This dude is gonna try the same thing with whoever he’s with. You were honest enough with yourself to say it to him. If he’s that loaded, whatever he purchased won’t be that big a deal.

  3. Brad says:

    BTW – I might be the perfect man for you – you don’t care about looks or money. I’m mudflap ugly and totally broke.

  4. Amanda Jillian says:

    Damn! I don’t know if I would have been able to turn down the trip. And I’ve been dying to see Wicked!

Leave a Reply

Your email address will not be published.

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>