Top 4 Dating Mistakes Guys Make

Posted by in dating after divorce, dating in midlife | 0 comments

dating mistakes guys makeWomen’s magazines and websites overflow with their analysis of dating strategies for women. Men’s publications devote maybe 1% to this topic. I want to correct the imbalance with this roundup of the top 4 dating mistakes guys make, reflecting the hard-won (and sometimes lost) knowledge of today’s guest blogger, writer Van Wallach, author of “A Kosher Dating Odyssey.”

Top 4 Dating Mistakes Guys Make

know when to hold em1. Know when to hold ’em/when to fold ’em. If you have months or years of time to kill, try becoming obsessed with a woman after a few good dates and perhaps even different degrees of physical contact. The calendar pages will fly by and you’ll have zilch to show for your effort except being another year older and even deeper in debt. Obsessing over a woman simply annoys her and torments you. You’re better than that. If a woman warns you, even after a passionate make out session, “I could bolt at any time,” believe her! That’s as clear a warning as a woman can give. As much as it hurts to stop calling, emailing and texting, if she’s not responding, cut your losses. She didn’t somehow lose all access to technology and is unable to reply to you. She’s sending you a message to cut your losses. I know this from both college and post-divorce dating experience where I churned around for years with yes-no-maybe so relationships. Move on to the next prospect; she’s out there. I like quoting a line from one of the second batch of Star Wars movies: “There’s always a bigger fish.” And let somebody else enjoy the one that got away. You’ll both be better for it.

don't be cheap2. Don’t be cheap. This is going back a long way, but in high school and my rogue male single days in New York in the 1980s, I constantly fretted on the cost of dates. I got this attitude from my mother, who grew up during the Depression. I saved a penny but I bought myself endless grief from women. Some strategic investment in little things – I’m talking about a cab ride late at night versus a subway ride on the dark scary New York trains to Brooklyn – would have gone a long. As a divorced adult with a steady white-collar job and no debts, I’ve moved well away from this attitude. Spend a little – on the gift, the nicer hotel, the cab, the theater tickets, the silken scarf instead of the toaster. Women appreciate big and little gestures. In the long run the investment, as part of a thriving and mutually healthy relationship, will pay off. You get out of a relationship what you put into it, and that includes investments that the woman makes in you. If the financial and emotional investment go mostly in one direction, then please refer to mistake no. 1. You may have other issues. But you’ll never get to the level of a strong relationship if you cut corners when you shouldn’t. My girlfriend and I celebrated her birthday to see a matinee of the new Broadway musical “Beautiful: The Carole King Musical,” followed by a private talkback with the author (a college classmate of mine) and a cast member. Expensive? I didn’t even think twice about it. She’s well worth it and the memories will last forever. The Russian Tea Room and tickets to a concert at Carnegie Hall? Sure, why not? I’m good for it, and I like this genuinely generous and giving side of myself that I couldn’t express so well in decades past. I’ll save the $9 tickets from TDF to see “Confessions of a Cuban Sex Addict” for later.

alchohol on a date3. Beware the alcohol demon. Go to any college campus or bar and you’ll hear tales of hookups, heartbreak and even criminal assault fueled by excessive drinking. While a glass of wine can set a fun mood when two wary adults meet for the first time, anything more can lead to fateful errors in judgment. Why? Because drinking clouds your thinking and loosens inhibitions, so you can’t evaluate a woman realistically. That’s happened to me, with major consequences. Getting mutually tipsy and acting on primal human instincts is a sure way to collect an invoice of costly regrets. Do you really want your dating life to be like an episode of “Girls,” waking up in a Brooklyn apartment not quite sure what went down the night before, wondering who that stranger with the tattoos is on the other side of the bed? Don’t do it! Save the screwdriver-driven intimacy for the time when you know good and well what’s happening, not when you’re trying to scope out a first or second date.

be bold4. Strap a pair on. This is the flip side of no. 1. Know when to hold ’em. If you see an opportunity, act on it. Introduce yourself, follow up on the dating lead from a friend, get in touch with old flames where romance never quite blossomed; sometimes, timing makes all the difference. What didn’t work five years ago might catch fire this time. You don’t know until you try. If Plan A doesn’t work, go to Plan B, don’t keep recycling Plan A (my earlier obsessive approach to dating, which led to frustration and loneliness). Maybe a friendship will result, maybe something else, maybe a tempting situation. Take the initiative, write the email, go to the event. What I tell people: Nothing ever happens if you’re sitting on your duff at home watching TV and eating ice cream. Get out there and make things happen, either on a dating site, MeetUps, volunteer groups, church or synagogue. Get out of your guy-pack to put yourself into new situations that may be outside your comfort zone of sports or drinking. So many social organizations these days are dominated by women (ever been to a book group discussion?) that being the male who shows up gives you visibility and huge opportunities. Crack open those Oprah Book Club materials and get ready for a dating adventure!

What mistakes have you made in dating? Can you add to this list?


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