5 Silly Mistakes Women Make When Online Dating

5 Silly Mistakes Women Make When Online Dating

Computer Crash


You wouldn’t believe some of the silly mistakes I see my clients make when online dating. Or, maybe you would. Maybe you’re making some of these same errors yourself. Most single women are scared that they’ll never find true love and that they’ll wind up alone.  My biggest fear was that I would find myself single with chin hairs and a houseful of cats at 80. The thing I don’t get is that, despite their fear of winding up alone, when I sit down at the computer to review online profiles with most clients I see them reject one good man after another for what believe are silly reasons. Below are some of the key mistakes I see my female clients are making.

1.  Eliminating men on unreasonable height requirements: I understand that we all have our preferences, but if you are a 5’4″ tall woman who likes to date super tall men: good luck.  No matter how physically attractive you are, you are shooting yourself in the foot because you are competing for the same men that every other woman is going for.  There are tons of wonderful shorter men who get overlooked because so many women are fixated on height. My husband was 2 1/2 inches taller than me.  With age that difference is growing smaller. Who cares? I’m married to a wonderful man who adores me. I will always look up to him. In my eyes he is every inch a man. Next time you are searching through profiles, set the minimum requirement at your height plus 2 inches. You can search as high as you want, just start lower. You need to get over the height thing or you might wind up alone.

2.  Basing too much on the photos: Tattoo this on your brain: You cannot put too much weight on the photos. Some will look better in person than they do in their photos and some will look worse. You need to keep an open mind. Also, while you don’t want to go into a relationship thinking you will change someone, many have never had the influence of a good woman to help them create a sense of style and they would welcome some input. You have to feel them out. I had a girlfriend who did a makeover on her boyfriend (who she later married). When they met I thought he was a bit of a slob, but by the time she was done with him, she had transformed him into a good looking man.

3.  Failing to be generous with men when they reach out: Very often a man will send an email that says, “Hey!” or “What’s up?”  Or, they might write “Hi.  I read your profile and think we might have a lot in common. Email me if you like my profile.” Many of my clients won’t respond to these emails because they are so generic unless they find a guy really cute. Then all bets are off. It’s sad, but, the more attractive someone is, the more we let them get away with. While these emails aren’t very inventive, you need to look at it from a man’s point-of-view. It’s intimidating to be the one to break the ice with a beautiful woman. And who isn’t afraid of rejection? It doesn’t hurt to be a little more compassionate with these men and cut them some slack. Next time a man writes a simple “Hi!” in an email to you, try being more playful and generous in return. He took a risk and got the ball rolling. You can throw it back. You might write something like, “Hey, you gotta do better than that to get my attention!” Or, you could say, “Thanks for reaching out…” and then mention a couple of things from his profile that you have in common. One of my clients simply wrote, “Type,” in response to a generic email she’d received. It worked.

4.  Not responding to a man’s email if he fails to ask a question in his email: I had three clients come in one day who had all stopped emailing with men who had responded to their emails without asking them a question about themselves. It was a shame because the men had actually taken the time to write very thoughtful responses to each of these women. When I thought about why they’d given these guys the ax, I realized that the women wanted the guys to ask questions so they would know what to write back. The thing is that men often don’t ask questions. It’s not how men communicate with each other. Women think that asking questions is the way to get to know someone. Men usually don’t ask questions with each other because they don’t want to pry. So, the next time a man doesn’t ask a question in his email to you, you can simply write back and say “Ask me some questions and I’ll tell you no lies J” or you can play off something they said in their email and apply it to yourself.  “You mentioned you went hiking this weekend; I take dogs hiking every Saturday. Care to join us?”

5.  Not initiating correspondence to the men you find attractive: Think of online dating as a virtual singles party.  At a party, you would never know who was checking whom out first.  You might spot some cute guy across the room and, the minute he looks at you, you look away. You’ll know who was checking out whom first. In 2014, it is perfectly acceptable in the online dating world for a woman to let a man know that she noticed him. And it’s a mistake not to.  I was at a party a few years ago where I met two different couples who had both met online—and both of the husbands bragged that their wives were the ones that made the first contact! These were all people in their 40s. So, get over old-fashioned idea it’s not okay to let a man know you’re interested, and start emailing some guys that you’re attracted to.  If you go for what you really want, you will have a much better chance of getting it!

Happy dating!

Looking For Love In All The Wrong Places? Try An Invisible Girlfriend


I’ve finally seen it all. Have you heard of the Invisible Girlfriend app? For a monthly fee, you can create your own fictional virtual relationship…and it’s enough to make Siri jealous.

This new service provides you with texts, phone calls, voicemails and will even give you a Facebook relationship with the invisible girlfriend of your dreams. Why might one need to create such a digital delusion? In an interview with Buzzfeed, Creator Matt Homann explained: “Our audience might come from a variety of situations: maybe they’re in a same-sex relationship they’re hiding from disapproving relatives, are trying to avoid the unwelcome advances from a coworker, or have chosen to focus on their work instead of romance.” I would also add that it could be used to make an ex jealous or to cover up the fact that someone suffers from social anxiety and isn’t able to get a girlfriend.

Read more of this post on YourTango.  Image from Invisible Girlfriend.

It Pays to Offer to Pay

NOTE: Very shallow DOF, with critical focus on edge of bill check.

We all have our fair share of questions when it comes to dating:  How do you start up a conversation with the smoking hot woman you just made eye contact with? Should you text a guy to thank him for a great date? How long do you wait to invite someone you’re wildly attracted to over to your place? One of the most common questions I’m asked—and one that can be the most uncomfortable of all—is who should actually be paying for dates. You might be surprised by the answer!

We’ve all been there—your head is buzzing from wine and too much forced conversation. The waiter comes and sets the bill down between the two of you and it sits there smoldering on the table like it’s radioactive. You’re not sure you want to see the person across from you again, but you still want to do the right thing. If you’re guy, you probably picked a place that was nice enough (and expensive enough) to impress a woman, if all went well. If you’re a woman, you might assume he chose someplace he could afford. Or, you might also be traditional and think that men should treat. The question is:  In 2014, should men still be expected to foot the bill for dating?

Let’s look at some facts.  In an online study of more that 17,000 single heterosexual men and women, Janet Lieber, a Professor at California State University, Los Angeles, found that while men are covering expenses 84% of the time, 64% of them expect their partner to chip in. Guess what?  44% of the women surveyed said that they were bothered by that expectation.

Ladies, sit down and do the math!   An average date cost $75-$100.00, no question, even when you decide to keep it simple with something like dinner and a movie. A movie ticket is an average of $10.00 a pop. Two drinks and a snack will add about $15 more to your tab.  Then, there’s parking (with those horrible validating machines). If you have dinner afterwards, there will be drinks, appetizers, a main course, a tip, and even more parking. If a man is dating actively, imagine how much money he is spending a month on dates—even if he’s only dating you!

Many modern women earn as much, if not more, than the men they’re dating—so why shouldn’t they at least offer to contribute? Younger less traditional men will probably accept the offer and older more traditional men are likely to refuse, but they will still appreciate the gesture.

A Naked Dater® knows that offering to get the bill is a great way to really impress your date. If you go to a movie, you might offer to get the popcorn and sodas, split dinner, or put the drinks on your tab. Not only is dating extremely expensive these days, but the gesture of offering to cover even part of the tab will make you seem appreciative and thoughtful.   And who wouldn’t want to be seen as considerate and generous from the very first date?

My advice?  Communicate openly about paying, even on the first date. You don’t have to do each other’s taxes at the dinner table, but offer to split the bill or pay for valet.   It’s a great way to show you appreciate his generosity and it will set you apart from the pack.

Recently, my client, Emily, declined an all too passionate kiss from her date after their third dinner together.  His response?  “If you weren’t gonna give me some, why did you let me pay for dinner?” Up until that moment, Emily had thought the date was going well, and she felt blindsided by his accusation. “Did I lead him on? I have no trouble paying for myself, but I’ve been reading all these dating books that say that the ‘feminine’ thing to do is to be receptive and let a man pay.”

There’s no question that Emily’s date was out of line, but she agreed that, in the future, she would offer to pay so that there is no question in a man’s mind that she isn’t trying to get something for nothing.

Is it a Mistake to Get Sexually Involved with a Man Who’s Recently Divorced?

intimate young couple during foreplay in bed 

Dear Lisa,

I met this wonderful man and we have been on 7 dates. It’s going really well.  I haven’t felt like this about anyone for a long time. I am totally smitten! He has been divorced about 3 months ago and has two young kids. On our third date, I asked him what he was looking for—something casual dating or a more committed relationship. He said that he is looking for something casual right now. I agreed with him and said that he should enjoy his freedom and date especially after having been married for so many years. Unfortunately, I am 35 and I want to get married and have a family of my own. He keeps asking me out, and it feels like we’re getting closer and closer. He even said that we could bump our dates up from once to twice a week, so I know he really likes me. The last time I saw him he cooked me dinner at his house and, afterward, we made out for over an hour. It was AMAZING. We have a very intense connection. I am pretty sure we’ll sleep together the next time we see each other. It seems like the natural next step, but I just wanted to hear your thoughts on the matter before I do something I’ll regret.




Hi Dana,

Congratulations on meeting such a great guy. I know it might seem like sex is the logical next step, but I would like to suggest that you take a step back and consider a few things first.

  1. You don’t know each other: You’ve been on 7 dates. If each of those dates was 3-4 hours, the two of you have probably spent a total of 24-28 hours together. That’s not a lot of time to really get to know someone. No matter how intense the connection is between you, you don’t know this man.
  2. Timing is everything: You want marriage and a family, and he is just out of a divorce. Then there’s the issue of kids: you would have to find out if he even wants more. He might be the greatest guy in the world, but if he just wants to date casually right now, you will be jeopardizing your dream of marriage and a family if you get more emotionally involved with him. It could be years before he is ready to be in another committed relationship. At 35, you don’t have time to wait around for him. You need to find someone who, like you, is ready to get married and have a family… and, yes, they’re out there.
  3. If you have sex with him, you are guaranteed to get hooked in: You admitted that you are smitten with this man. If you have sex with him, you are going to get even more attached to him and it will be even harder for you to let him go if it comes to that.

I am not telling you end the relationship, but I am suggesting that you talk to him about these things. Tell him that you genuinely don’t want to put pressure on him. You think he should be dating casually right now. But also tell him that you are 35 and you are ready for marriage and family. Say, “I know myself. The way I am feeling, if I have sex with you right now, I am going to fall for you and want some kind of commitment. The romantic in me wants to believe that it will all just work out, but the realist in me knows I will be putting my dream of having my own family at risk if I spend time pursuing this when we are at different places in our lives. I would love to hear your thoughts.”

Gook luck! I would love to know what happens.

With love,



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