Think You’re Un-Dateable?

Feel like your dream woman will never appear? Here, some sage advice for guys who’ve lost hope and swear they’ll remain single forever.

By Phineas Mollod and Jason Tesauro

tuck in a dateless pit? Whether your celibate season stems from a spate of “first date and done” failures or you haven’t had one semi-serious relationship since Bill Clinton was in office, we’ll have you back in the game before Hillary or Obama is kissing babies in New Hampshire. With a little fine tuning and an attitude adjustment, the new, improved you can be back on the scene by next Saturday night.

Play up your best assets””
Whether you’re tweaking your profile online or polishing your date-night conversation skills, reinventing yourself doesn’t mean starting from scratch. Even
Rather than obsessing over finding your ideal date, scan for dynamic up-and-comers.
the most so-so sort has assets and charm, serviceable skills, and something interesting to say. Identify these strengths and bring them front and center. Modesty got your tongue? Ask your friends what your most dateable qualities are. Are you a good cook, did you learn how to ballroom dance in high school, or can you figure out how to fix just about anything that needs fixing? All very desirable assets that can easily get overlooked. On dates, make sure to place yourself in venues where you excel; if you can play a mean game of tennis, off to the courts you go. Otherwise, strategize ways to drop mentions of your skills into casual conversation… or weave them into your profile.

Up your fascination factor””
Every guy has shaken his head upon spying a superbabe on the arm of an average Joe. Why is she with him? The odds are three to one that it’s because his life is dynamic, and she likes swirling around his irresistible force like a sprightly electron. In short, an interesting dater has an interesting life. Thus, it’s time to trade primetime TV for more intriguing endeavors that’ll up your sex appeal. Identify your anti-social hobbies (obsessive Xbox playing), and try to adopt some lover-friendly ones. Compare boasts about swashbuckling in virtual reality with these endeavors: gym classes (kickboxing, rock climbing), learning guitar/Japanese, volunteering for a charity, or taking a painting or poetry class. These are all great conversation-starters. Need a jumpstart? Seriously bone up on something and steer date night conversation to that topic. A few hours of studying later, your simple interest in astronomy brightens al fresco dining (“I’ve just gotten into stargazing. That bright clump right there is the Pleiades, representing seven sisters forever chased by Orion. How many sisters did you say you have?”).

Make an effort with your image””
Tiny makeovers — a new haircut, creative facial hair, a new shirt or two, Italian shoes — make for a grand first impression and prevent the sinking feeling that even the polyester-uniformed waiter is dressed better than you. Moreover, men who greet their dates with wrinkled duds and slumped shoulders communicate a lack of potency and effort. Especially compared to a put-together lass who invested an hour into her candied outer shell, your smoothed-out bed head + ungainly stubble + tired office clothes = a dateless schlub. If you’re dating online, update your profile regularly since some lady may be eyeing you from a distance but hasn’t yet sent a hello. Showcase your new and improved, non-static life by changing headlines, photos, and interests to reflect your own steady progress.

Broaden your search””
Think of it this way: Applying to your dream college was an admirable task, but the prudent student also sent off applications to a few safety schools. Same goes with dating. Widen your search parameters when you look online or while you’re out on the prowl, and you’ll enjoy a net gain in confidence and positive responses.
On dates, make sure to place yourself in venues where you excel.
It’ll surprise you what hidden gems are lurking behind funny photos or others whose shining personality overshadows what might be deemed minor physical imperfections. Rather than obsessing over finding your ideal date, scan for dynamic up-and-comers (just like you, right?). The more you date, the more confidence you’ll gain.

Give your life a more positive spin””
Nothing is less sexy than negativity, so make sure what you say about yourself remains upbeat. Responses about work should be more than, “It sucks, but it’s a paycheck, right?” Similarly, portray your weekend activities as lackluster (“Saturday night? Yeah, I did laundry”), and see how excited your date will be to spend a future one with you. Likewise, make sure you say a few positive things about your date too, whether that’s a swoon-worthy “You look beautiful tonight” or “I find your insights on solving our impending oil crisis fascinating.”

Don’t reveal too much””
A date is not a therapy session (and hopefully lasts longer than 50 minutes), and should the question of prior relationships or hardships arise, ditch the sob stories. There’s a reason that guys in healthy relationships often receive attention: People feed off the scent of victory and poise. Be sincere without coming on too strong, and practice brevity. If pressed, spin it delicately. Limit yourself to a concise two-minute drill that efficiently and assuredly touches on romantic failures, family crises, or bad history without date-sapping, pessimistic drama. Similarly, no one needs to know the last time you had a date. The honest and uncomplicated (“I’m really enjoying sitting across from you”) sure beats self-effacing pap (“Wow, it’s been so long… is this how a date feels?”).

Lastly, never initiate chatter about exes. Fellow XY chromosome bearers may commiserate with your tales of “my rotten ex,” but rest assured, a woman who hardly knows you likely won’t side with you. If the subject arises, chalk it up to a learning experience, not a grave injustice. Your language should be optimistic and upbeat: “On the other side of a six-year relationship, I learned a lot, I’ve changed a lot, and I’m excited to be out there again. Heck, my luck must be changing already since I’m enjoying an evening with you.”).

Phineas Mollod traded his J.D. for the editorial life and is often found riding the congested E train with his wife and daughter in New York. Jason Tesauro pushes pen and ink by day and leads the lifestyle seminar series by night, ne'er far from his sweetheart and a Brady Bunch houseful 'o tots in Virginia. Together they are the authors of The Modern Gentleman: A Guide to Essential Manners, Savvy and Vice and The Modern Lover: A Playbook for Suitors, Spouses, and Ringless Carousers.
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