My first date: a series of 7 unfortunate events!

Posted by in dating a dangerous man, dating after divorce, dating in midlife, first date success, online dating after 40 | 0 comments

first dateIt was a first date from hell, but it didn’t have to be. ‘David’ (not his real name) made his first mistake on the phone. We had exchanged a few emails on an online dating site. He called me and left a voice message. I called him back the next day… and he had no idea who I was. “Sandy? Refresh my memory. What’s your screen name?” Really? He had just called the day before. Couldn’t he keep his women straight? That was his first bad move. “What, are you in contact with twenty women and you’re waiting for them all to call you back?” “Something like that”, he replied. That made me feel very special!

He looked me up on the dating site and made his second mistake. “Oh, you’re pretty. The pretty ones never call back.” What?! First, he can’t keep his women straight; next, he sets himself up as a loser, unable to attract nice looking women.

But, I believe in giving men the benefit of the doubt. Perhaps he was just nervous. We ended up speaking for about a ½ hour, and I found him to be bright, engaging, and very cultured. So, I said yes to a date the following Sunday.

My first date: a series of unfortunate events

I was a little taken aback when I saw him through the restaurant window; he was much older than he appeared in his photos, shorter and more overweight than I expected. But those things don’t really matter as much as the energy and connection you feel on a first date. He did have nice blue eyes and a warm smile. I was open to seeing how things progressed.

He had invited me to brunch, so we went to the counter to order our food. He asked if I was hungry. Yes, I was starving. He was not. He had already had a big breakfast, and he only wanted coffee. But he told me I should feel free to order whatever I liked.

Unfortunate event number 1: Don’t invite someone out to eat if you’re going to eat before the date. Awkward! I was too hungry to care, so I ordered an egg sandwich and a coffee.

My food arrived, and because he had chosen a couch instead of a table and chairs, I made a freakin’ mess of my sandwich, getting crumbs all over my lap. Oh, well. I was beginning to not really care.

Unfortunate event number 2: Don’t sit on a couch if you’re going to be eating. It’s hard to be graceful with a mouthful of egg and bread, brushing crumbs off your lap every few minutes. And it’s equally hard to eat while being observed by your non-eating date.

Unfortunate event number 3: We immediately launched into a conversation about religion. He had extreme views on God and religion, and I was actually interested in hearing what he had to say. But then it got to be too intense for me, and my mind began to wander. I started to glance at my watch, wondering when the date would end. I would advise against having conversations about religion, politics, medical issues, ex bashing, or sex on a first date. Keep it lighter. Focus on shared values and fun experiences, and try to have a few laughs. That would be a good goal for a first date.

Unfortunate event number 4: When I returned from the ladies room, he said, “You’re very youthful. I’m probably too old for you.” Bad move. He was only about 7 years older than I am. I don’t mind older men who are youthful and energetic. I do mind older men who have poor self-esteem and self-sabotage throughout the date. Which brings me to unfortunate event number 5.

Unfortunate event number 5: He mentioned that most women who hear what he does for a living don’t want to date him. I said, ‘I knew what you did, and I’m here, aren’t I?’ Sheesh, stop putting your foot in your mouth, David!

Unfortunate event number 6: He said, “I don’t make a lot of money. Russian women only want to date men who make a lot of money.” He then proceeded to share a story of a Russian woman he recently dated, how pretty she was, how he slept with her, and how she left him because she wanted someone with a lot of money. First of all, TMI! Don’t share your sexual escapades about another woman, especially on a first date. Second, stop talking about women who reject you. It makes you sound pathetic. Why would I want to date the booby prize?

Unfortunate event number 7: He told me he had a great time and wanted to know if I’d see him again. Awkward moment. I thought my body language was pretty clear; I did not want to see him again. But, I also didn’t want to be unkind, and I was caught off guard. I told him that I needed to process the date and would let him know. Yes, it would be great to be more honest in the moment. I’m working on it.

* If a man asks you out for a second date at the end of the first date, and you’re not sure you want to date him again, don’t feel compelled to answer in the moment. You might want to mull it over. When you get home, you may realize you had a better time than you thought. If there’s enough reason to go out again, you’ll feel it in your gut. I knew this guy was not for me.

So, when he called a few days later, I told him I didn’t think we were a romantic match. He was gracious about it.

The truth is, this guy is bright, cultured, interesting, and good-hearted. If he stopped sticking his foot in his mouth and putting himself down, he may have landed a second date with me. And he would probably attract a lovely woman.

The moral of this first date story is, be your best on a first date. Don’t put yourself down, and make sure your stories aren’t about hot topics like sex, politics, or anything with a negative connotation.

Confidence is sexy. If you want to attract a confident partner, show up and be your most confident self throughout your life, but especially on a first date. You may not get another chance to make a good impression.


For a copy of my FREE report, “The Top Three Mistakes Midlife Daters Make (and how to turn them around to find love now)” please click here.

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