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Ask The Good Enough Guy: Dating And Desperation



Hey Will,

I need some Good Enough Guy help!

I’m in my early 30’s, educated and make a good living – and yet I am still single. I have my fair share of first dates but they never seem to materialize into a second, much less a relationship. Am I telegraphing “needy”?

Please help!

Toni, Detroit

Hey Toni,

Well, the only way for me to actually know for sure what you are telegraphing is for you and I to go out on a date, so I’ll pick you up around seven; I’m thinking dinner and dancing.

Just joking; my wife frowns on me dating, and I don’t dance unless I’ve been drinking, the Ravens win, or both.

Are you telegraphing “needy”? Maybe…but that’s not necessarily a bad thing.

*MAN FACT* Men need to feel needed.

Ask a man what would happen if he didn’t show up for work tomorrow and he’d probably tell you that the place would fall apart without him. He doesn’t just go to work for his pay check; they need him there. Ask him why he doesn’t miss a minute of his favorite football team’s game. He doesn’t just watch for the enjoyment; if he’s not there to support his team, they don’t stand a chance!

As a matter of fact, to hear the average guy tell it, it’s a wonder that anyone in his circle can even tie their shoes without him holding the knot. His mom needs him to run some errands, his brother needs help moving this weekend, he has to go and talk his friend off of a ledge. Most guys are just a cape and a blue Speedo away from fighting the forces of evil in their spare time.

And, if you don’t need him, where do you fit into his circle?

Maybe it’s just me, but there seems to be an awful lot of women these days singing the “I don’t need a man, I can do it all by myself” song, which is a good song to sing… if you want to do it all by yourself. I have no doubt that these ladies can and do take care of themselves, but I don’t think they realize the effect that “telegraphing” that fact, or actually stating it as a fact, has on a man. To us, “I don’t need you” means “you are of no use to me” which is just a stumble away from saying “you’re useless”, and by that time, we have our coats on and we’re thinking about how cute the waitress was.

Now, as I said before, you didn’t give me much to go on as far as what you’re doing wrong, but you’re first sentence said that you’re in your early thirties, educated, and make a good living. Just between you and me (and the MILLIONS that read this blog) I’d suggest that, on a date, you not open with any of those three facts. And even though I know I’ll get some hate mail over it, I’ll explain why:

– “I’m in my early thirties…” -Never tell a man your age unless he asks, which a gentleman never does. (catch 22!)

– I’m well-educated…” If you tell a man how well-educated you are, he will either try to impress you with how well educated he is, or try to change the subject so you don’t realize how uneducated he is… and do you really want either of these?

– “I make a good living…” Unless you’re hoping to get to pay the check, talking money or trying to look like, act like, talk like, or even pretend like you are completely self-sufficient is a worse mistake than looking needy. Showing up in a diamond tiara is as bad as showing up bare-footed in a potato sack with a sign around your neck that says “helpless”.

So, what should “telegraph”?

The simple answer is COMFORT.

You sound like a very capable, eloquent, attentive, efficient, women… and any boss would love to hire you… but you aren’t going on job interviews; you’re going on dates. There is nothing comfortable about a job interview; the applicant is usually so nervous that she makes the interviewer uncomfortable. This is to be expected in an office, but not at a TGI Fridays

*MAN FACT* Make a man comfortable enough, and he’s putty in your hands. (This stuff I’m giving you is GOLD! Don’t waste it.)

I don’t care what anyone else tells you, a comfortable man stays where he is. If you want a second date, be confident and comfortable enough that he can be comfortable with you on the first date. Don’t pull out your patented hair-flip, lip-bite, with the giggle chaser… he’s gonna think you’re having a seizure. Don’t try to telegraph, send signals, or do hand or eye signals… he’ll think you’re telling him to steal third. (Seriously, we aren’t good at that stuff). Don’t do what you normally don’t or do what you normally wouldn’t.

Instead, be the REAL YOU. (The dressed-up, cute, REAL YOU, not the REAL YOU that wakes up in the morning, yawning and scratching.) When he talks, listen and be interested. If he doesn’t talk, then you talk, and be interesting. Laugh at his jokes, but not like he’s Chris Rock. Tell a joke of your own, or a cute story, or anything that keeps things moving in an entertaining direction. This guy wants to feel like he’s winning you over… so let him. Enjoy yourself. Enjoy him. Enjoy being with him. And if you can’t, do you really want a second date? If he’s too much of a waste to deal with, order the lobster, put your doggy-bag in your purse, put on your coat, and think about how good-looking your waiter was. Then… go home and make another date with a better guy for tomorrow night.

Us guys aren’t looking for a wife on our first date; we’re looking for someone we enjoy that seems like they enjoy us too. I’ve never called a woman back because of how well-educated she was or how much money she made, but for almost everyone that I ever did call back, the conversation started with, “Hi, this is Will. I had a really great time with you the other night…”

If you seemed a bit needy, he’ll soon forget that… but if you two laughed so loud that the manager asked you to quiet down, he won’t forget that… and he’ll want to do it again.

William Jones is originally from the tiny town of Alton, Illinois, and now lives in the tinier town of Reisterstown, Maryland. He is a happy husband and a proud father of three, and writes as a hobby, in those few, spare moments he finds between husbanding and daddy-ing.


  1. M.E. Johnson

    February 19, 2011 at 12:45 pm

    Good stuff, Will (I’m your fan anyway). I wonder… there must have been a time when she wasn’t so into getting married. So what were her dates like then? Perhaps a trip down memory lane would be helpful.

  2. Auntie Lisa

    February 19, 2011 at 1:02 pm

    From my own experience (and I seldom had a second date until I married at age 42), the problem wasn’t so much being seen as “needy”, but more being seen as an easy catch. Too eager maybe. Guys like the thrill of the chase and the harder they have to work to win you over, the more highly they value you.

    My husband is always bragging how hard he had to work to convince me, a California native, to even consider a relationship with this guy I met online who lived clear over in Texas! 😉 I wasn’t playing games, either… it was genuinely a tough sell. But he convinced me, and we’re now both extremely happy about that. 🙂

  3. Jacki Marie

    February 19, 2011 at 1:10 pm

    another good one, Will.

  4. Will Jones

    February 19, 2011 at 1:48 pm

    M.E.- “BIG THANKS” for being a fan! I think you’re right. Taking a little time to look back can be a big help in moving forward. I think the big push to get married around thirty is another one of those “biological clock” situations… and if men have those clocks at all, they must have a really small face and a really big snooze button on them.

    Auntie Lisa-There’s definitely something to be said for the thrill of the chase, but I’m betting, if you were still on the market at 42, it was because you weren’t willing to settle, and I’m betting your husband is extremely happy about that too!
    I always look forward to reading your comments… you crack me up!

    Jacki- Thank you for the compliment!

  5. Auntie Lisa

    February 19, 2011 at 2:41 pm

    Haha… snooze button on the biological clock! That’s hilarious, Will! Great of putting it. It’s either that or men’s bio-clocks are set to a radically different time zone, being that men remain fertile much later into life.

  6. Auntie Lisa

    February 19, 2011 at 2:46 pm

    I meant “great WAY of putting it”…

  7. Rene Syler

    February 19, 2011 at 3:14 pm

    And going on 5 years of wedded bliss right? The online dating thing is a topic I want to explore as well. I think if you want to be married you need to be honest with yourself and up front with the people you date. That’s not desperate; that’s focused, LOL. My sister met her husband online as well, as did my daughter-in-law. They’ve all been happily married for years!

  8. The Broke Socialite

    February 19, 2011 at 3:33 pm

    Steve who?

    P.S. GEM: Mr TBS and I met online nearly 12 years ago and before it was socially acceptable. I’m not going to tell you how long we kept up our farce before spilling the beans to our immediate families.

  9. Auntie Lisa

    February 19, 2011 at 4:03 pm

    The online dating thing would be a fun topic! Yes, the attitudes have changed somewhat about that over the years. It used to be viewed as only-for-the-desperate! haha

    (We’ll hit 6 years in April! How time flies…)

  10. Rene Syler

    February 19, 2011 at 4:41 pm

    @ The Broke Socialite: bwahaha LOVE IT!

  11. Rene Syler

    February 19, 2011 at 4:45 pm

    @Lisa: 6 years already?? Wow.. Congrats! It’s funny, I don’t think of it as desperate as much as I think “who on earth wants to waste time trolling bars and ‘hoping” the person you meet isn’t a dud and that you find out if he is before you invest a significant amount of time in him?” The other thing is frankly how, given the geographic distance between you and your spouse, would you ever have met? And the great thing about online is that you know and have common interests before you even meet. I love it when people say ” yeah but you don’t know who you’ll meet.” Oh I think you probably have a better idea this way than the bar scenario.

  12. Auntie Lisa

    February 19, 2011 at 4:57 pm

    While there certainly are red flags to watch for, I think they are easier to spot in the online scenario. (I could go on at length about this…) But you definitely hit the nail on the head… the bar scene is a crapshoot. Big time-waster. Doing it that way, it would take years to screen out the losers and find one worth dating… where online, you could screen (literally – ha!) 100 guys in one evening… in your pajamas! You quickly learn how to read between the lines on the guys’ profiles and can easily cull it down to the few that might be worthwhile for you. Once you do, you can communicate in writing however long you need to until you feel comfortable talking on the phone, then meeting in-person.

  13. Kim Wright (Pinkim)

    February 19, 2011 at 11:22 pm

    Wow, so true, this is GOLD, and very well written to boot…you know, I started wondering at the Ravens comment and then you mentioned Reisterstown, MD..You won’t believe this, but I too reside there! How is that for a small world?

    Great advice and well delivered.

  14. Nikki Newman

    February 20, 2011 at 1:05 am

    Fantastic piece, Will! So enjoyed reading this. I love your advice. I met my now husband 9 years ago online after a colleague recommended it. We met very soon after I first registered and had a good few months dating via email and phone call. It was amazing. But I wanted to add, that I realised I’d been going for the same type of guy over and over again, and wasn’t getting anywhere, so I challenged my ‘ideals’ – which to be honest had had me wasting a lot of time with some really awful guys – and found my soul mate.

  15. Will Jones

    February 20, 2011 at 10:18 am

    Kim- It’s amazing how that works! I met one of my really close friends on-line and found out later that we’d grown up less than four blocks apart, but we’d never met! As “tiny” as Reisterstown is, I’m sure we’ve seen each other around, and if not, we’ll have to make a point of doing so! Thank you for the great compliments. I really appreciate do them.

    Nikki-So funny that you mention the “challenging ideals” thing. After my best friend had had a string of bad relationships, I ask him what he wanted in a wife. After he ran down a short list of the usual attributes, I asked him what he thought he NEEDED in a wife. The look on his face changed… and so did the list. (About a year and a half later, he was married, and he has been for the past five years.)
    I can only speak on it from a guy point of view, but we, as men, tend to want someone with the same skill sets and shortcoming that we have because we think that will make the person easier to get along with and that we’ll have more in common with them. But if both love to shop, who’s watching the money? If both love to talk, who’s listening? If both are dreamers, who holds the other’s feet on the ground? “Challenging ideals” is a GREAT way to put it, and you’re right on the money (but you and your soul mate already know that!).

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