Dating Advice for Men


I’ve been back in the dating marketing for several years now and let me tell you, it is a jungle out there. I’ve gone out with men who are everything from financial advisors to scientists to private investigators to chefs to engineers, you name it. I have found that people are often entertained by the wild stories that I share, so I thought, why not write about it. For your reading pleasure, may I present to you the first of many blogs on my dating life:

6 Dating Tips for Men

#1 Don’t Go to Jail on Your First Date

I was a newly single woman in her late 20s and I had decided to download Tinder. It was a welcomed distraction as I was still healing from my divorce and like many people who have just come out of a long relationship, I wanted to prove to myself that I still “got it.” So I started talking to a few guys and one of them seemed really interested in me and we had a lot in common, so we finally decided to meet for drinks. This was so early on and I had no idea what the dating etiquette was anymore, so I was nervous to say the least. We were going to meet on Wednesday after work, so around noon that day I texted him to see if we were still on. I heard nothing. 4pm rolled around and I texted again. Silence.

Why would you pretend to be into someone just to blow them off at the last minute? And he didn’t even have the balls to cancel? If he didn’t want to meet up, he should have just told me instead of choosing the passive aggressive approach of not even texting back. So childish. This is why I hate dating, I hate these games, why can’t people just be honest.

Wednesday came and went and I still heard nothing.

But then… one week later, I got a text. He started off my telling me that he thought about lying, but wanted to be honest with me in hopes of mending some of the mess. He said that he was sorry he stood me up last week, but…you guess it.

I got stood up on the first date because the man was in jail.

He told me some jumbled confusing story about how he had all these outstanding tickets and got pulled over and went to jail, yada yada… but the best part was that after the long text chain of explanations, he asked if we could still go out sometime.

No, sweetheart. We won’t be going out.

#2 Don’t Say Anything Negative about Her Appearance

This seems like a no brainer, right? I mean, come on. Everyone knows that the last thing a girl wants to hear is something bad about the way she looks. Even if you are joking, just don’t do it.

I was on a second date. The first one had gone well. He had taken me to brunch at Three Sisters Café, which is one of my favorite spots. Now we were at Iozzo’s, a romantic little Italian restaurant just south of downtown in Indy. He was doing well so far – cracking jokes, asking good questions, listening. He had beautiful icy blue eyes. I found out that he was really into film so we were talking about actors and actresses and I happened to mention that sometimes people said that I looked like Alyssa Milano. He was quick to respond, “Ohhhhh… well… yeah, but she is way hotter.”

It gets better.

So then he continues into a monologue about his past girlfriends and how I rank in appearance against all of them. Supposedly the last girl he dated was not as hot as I was. She was also a brunette. But the girl who he dated in Florida, who was a Disney princess at Disney World and was blonde – she was definitely hotter than me. “Now that I think of it, she’s probably the only person I’ve dated who is hotter than you. But you’re definitely the hottest girl I’ve seen on Tinder.”

Face palm.

There was no third date.

#3 Don’t Steal Someone Else’s Identity

There are certain people who ask me out where there’s something in my gut telling me not to go on a dinner date with them. I realize now that this is a sign that I should not go on any date with them, but at the time, I thought that this gut check just meant I should grab drinks and scope him out before committing to a full meal.

So I went out with this man, we sit down, order our drinks and start talking. The first pause in the conversation he says to me, “Some people are intimidated by my size. I mean… I’m so big and tall. I hope that doesn’t bother you.”


I ignored the comment and change the topic of conversation by asking what he did for a living. He told me that he is a financial advisor and is making six figures working for himself and also travels all over the country doing so. He doesn’t usually stay in one place for very long, so this may be the only time we get to hang out.

Oh brother.

I end the date prematurely and texted a mutual friend to give her an update on how it went. He’s kinda creepy right? Yeah, a little bit more than kinda creepy. Three weeks later this mutual friend texts me and says, “Hey, so remember that guy you went out with? Yeah so… he went to jail for identity theft. I knew something was off about him. Guess you dodged a bullet on that one.”


#4 Do Share Your Horrible Date Stories

There’s nothing that lightens the mood better than swapping terrible date stories with your new fling. That’s a sure way to make me laugh and it’s a fantastic ice breaker. It’s also a way to remember that everyone else is also trying to navigate this crazy thing we called love.

One of the guys that I went out with told me a story of his very first date after his divorce. Understandably, he was nervous about the date, just getting out there for the first time in a long time, but they had been texting a while and he was interested in her. They sit down at dinner, enjoy some small talk, then… out of the blue… she says, “hey, so I’m pregnant.”

The guy puts down his fork. Pauses. Leans in. Looks her in the eye and asks… “Is it mine?”

At this point in the story I’m pretty sure I snotted beer out of my nose because I was laughing so hard. I guess she didn’t think it was as funny as I did.

#5 Do Bring Her a Present

I know I’m speaking for more than just myself when I say that women like presents. It might feel old fashioned or seem like you are trying too hard, but I am telling you – the odds are in your favor. If you bring a present and she is mad about it, I’ll reimburse you.

One of the best presents that I received on a first date was flowers. Not fully bloomed flowers, but flower seeds to plant in my tiny garden boxes on my deck. It was spring and such a thoughtful present. Despite my lack of a green thumb, I love plants and flowers and greenery. Extra points for creativity. It came with this note:

Image 1

I LOVE notes. I find them so enchanting and like they are little piece of your heart that you are sharing with the other person. It is created with your words, original thoughts, and meant to be just for one person. If that doesn’t make a girl feel special, I am not sure what does.

#6 Don’t Fall Apart If Things Don’t Work Out After the First Date

Le sigh… I’m just going to put this out there. If you are in love with someone after the first date, there’s probably something wrong with you. I’m sorry to burst all of the “love at first sight” bubbles, but movies aren’t real life.

We were at a restaurant sitting in a booth. I started to be concerned when he asked if he could sit on the same side of the booth as me. Warning bells went off. He was a nice guy, but a little too handsy and a little too much talk about when he can come over to my place to “see my artwork.” There just wasn’t any chemistry and it ddin’t feel right. So we texted a bit the next day and I explained to him that I didn’t think it was going to work out.


He told me that I wasn’t being fair, that I hadn’t even given him a chance. How could I do this to him? Can’t we meet just one more time? Talk to me. Tell me what you’re thinking. Stop ignoring my texts. This can work. We’re a great match. What do you need me to do? I’ll do anything! Lara. Lara. Lara. LARA. LARAAAAAAAAA.

Oh boy.

That’s not romance, fellas. That’s just bat shit crazy.

3 Replies to “Dating Advice for Men”

  1. So, here’s an ugly truth about #2. There’s a name for what he was doing-it’s called “negging” and it’s something terrible people do to try and sleep with women.

    In short, you tell a very beautiful woman she is not. You play off her inner fears and drag her down in the mud with you. It doesn’t work with confident, self assured women, and that’s why it doesn’t work with you. Your gut reaction was not to try and get his affection by sleeping with him, but sadly it works often enough that there is a large community of awful people trying this. It was made famous by an author named Neil Strauss in his book “the game.” It’s a book so awful that it has the audacity to be leather-bound so it will look like a bible on your shelf.

    I suggest to my female friends to read it-not because I think it’s worthwhile, or quality (it’s written like the first draft of a magazine article. (If that magazine were Highlights for children. (Written by a child. (But about manipulating women.)))

    It’s awful, but at least be aware-these people are out there and this is but one of their sleazy moves.

    I don’t do this. I have my own sleazy moves. Like paying attention and making a connection and respecting a person as a person. But I can’t give away all my secrets yet….

  2. Love this! Reminds me of when I had a coffee date with someone, and I could literally visual his “wife to be” checklist above his head. First round of questions were, “Do you like to cook?” “I like pie, can you make pie?” and, “Do you like children?” etc….
    It was terrible…… but also funny. The funniest part was later I heard that he was really confused why I kept declining to go out with him again. Poor, clueless thing.

    Well, the wife checklist is not a great way to start off a first date. A little too serious for me.

    1. I TOTALLY hear you, Mikaela! Some dates just feel more like interviews than getting to know each other… haha.

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