General Dating Questions/Frozen love life


Since you're writing a book called 200 dates you obviously know how to get a date. I am hopelessly bad at that!

My love life has been cryogenically frozen for the last eight years and I am SO ready for a change.

During the past few years I've tried to get a better grasp on dating by reading books, blogs, listening to podcasts, dressing better/differently, being more friendly and upbeat, being more flirty or even pretending to be an airhead. I used to go out dancing 4-5 nights a week and that never did anything for me. I have looked inside myself to see my shortcomings and become a better woman.

I talk to several thousand people at work every month and many of them are men. Maybe I am wrong, but that seems like more than enough opportunities to find a date or get laid. I haven't been on a date or had sex in almost a year.

People tell me often that I am beautiful or that I have gorgeous eyes or amazing hair. When I was in my early 20s (I'm 28 now) it was not uncommon for people to ask if I was a model. I have always been physically fit and healthy weight. On the negative side, during the last few years I have been mistaken for a man six times, which is disturbing.

Just for the record, I do not think of myself as an amazing beauty and I am not an ice cold princess. I always want to look presentable, but I lost confidence in my looks over the last few years, so I don't make much effort to look hot anymore. My clothes are always casual and flattering.

I am starting to conclude there is something wrong with me and that I should just accept that I am always going to struggle with relationships or be alone forever. Obviously, I don't want to accept that reality or I wouldn't be writing this question. That being said, I need to deal with this issue because it is eroding my confidence and I no longer have any desire to put forth effort in this part of my life. I have been stuck for a LOOOONG time. Would I be correct to say that these problems are not typical for someone in my age group? What else could I do that I haven't tried (and yes, I thought of online dating)? Is there something I am obviously doing wrong that I haven't noticed?

If you could give me the most honest feedback possible that would be great.

Hope your book is coming along well!

ANSWER: Hi Bella,

Let me start by saying that you can absolutely have whatever you want when it comes to dating. Lets unfreeze you. It takes a bit of effort, but If you want to find someone it is relatively easy to do. It has to be something you focus on like work or a diet.

You are in a rut and being confused for a man once not a problem, but six times and we have an issue. You need to look like a million bucks. Dress better, it makes you feel great and more confident. People feed off of how you feel about yourself. You should want to look you best everyday because it feels fantastic. I make sure I feel good with what I'm wearing even if I'm just going to the grocery store. You never know who you are going to meet.

It is all about statistics and even though you talk to several thousand people doesn't put you in position to date them. Lets make the process of meeting people as easy as possible and get you online. It is 2013 and 50 million people in the US are doing this.  Online dating is so easy because you have so many people to choose from and they are all looking to date. So get some photos professionally done. Great photos make the profile especially for women. Write something fun and original. Make sure go to a pay site like match or eharmony because the type of person will be a notch above the free sites. It is not always the case, but overall it definitely is. Make sure to see if things are working and tweak them if they are not. Most of my clients that fail have some obvious problems and blame the site, but 95% of the time it is there profile. You should be dating 2-3 times a week until you find someone special. Online dating is easy to meet someone hard to find the right one.

Bella, break out of the rut and take some chances. You can and should have an active dating life, but it is up to you. I am rooting for you.

I hope this helps,

---------- FOLLOW-UP ----------

Thanks for sharing your thoughts.

Starting way back in 3rd grade kids on the schoolyard used to call me a man, so this is not a new theme for me, I just hadn't heard it in my adult life until recently. A few years ago my friend had cancer and everyone in my friend group shaved their heads in support. Even though I had a shaved head and didn't wear make up nobody confused me for a man. People thought I was a lesbian, but that's besides the point, at least they could still tell I was a woman!

Anyway, yeah I know I could do online dating. I need help more with attitude than methods. If you have some thoughts on that I would love to hear them.

I got burned out on trying to meet guys after years of feeling clueless and being played. I resigned myself because I got tired of wondering why some guy wasn't feeling it for me and I just wanted to feel self-assured and focus on more important things in life. I have a BIG personality and wanted to be able to express it exactly as I chose, without regard for how potential suitors would view me. At that point in time, I felt I constantly had to check myself and make sure I was being sweet, nice and feminine and I didn't want to do that anymore. It was driving me nuts. I just wanted to be myself. Unedited.

I make half-hearted efforts to flirt with guys now, but the spark that once made it fun for me has disappeared. I have become very confused about how my looks and personality are perceived and I've totally lost confidence. How can I be beautiful and also be mistaken for a man? Does this just mean I am weird looking and some people happen to find it intriguing lol?

Anyway. Now I want to start dating again but I can't motivate myself to change my attitude. Also, do you think 2-3 dates a week is the norm these days? I don't even see my friends that much!


ANSWER: Hi Bella,

If you don't want to play the game don't play, but you can't expect to find someone unless you play. You just have to be smart about it. First off if you are serious about finding someone you have to make it a priority. Yes, you have to date a lot of people to find the right one. I hope you find the perfect person after one date, but it rarely works that way.

The real question is whether you are open to doing the things necessary to finding a great guy. If you half ass it you will end up with a bunch of losers and be jaded about the whole dating world.

What guy wants to be with someone who isn't sweet, nice, and feminine? You can be yourself and let your personality shine, but you have to present yourself in an appealing way. You have put forth some effort if that is what you really want. It sounds like you had some bad luck with some guys that weren't right for you and you pretty much threw in the towel. I think you can turn it around pretty easily.

I have had clients in the same mindset as you and we work on their attitude, but we end up changing a lot more. People fall into a bunch of bad habits and it affects every aspect of their life not just dating, but careers and other relationships. If you really want to do it right you need to commit to change.

Dating is so much fun and I miss it. I'm in a great relationship but, a part of me would love to be in your shoes.


---------- FOLLOW-UP ----------

QUESTION: Saying that I need to commit to change is logical and I totally agree with you. But, what actual steps do I take to fulfill this commitment? Just saying that I am going to start dating again will not solve my issues of bitterness and anger towards men AND my dating skills will be no better (probably worse actually) than when I initially stopped dating. Doesn't this just set me up to have a relapse? You don't need to give me step-by-step instructions, I am just curious what it means to "commit to change" from your perspective?

Dating skill is like any skill, it comes with practice. That is why going on 2-3 dates a week will get you up to speed relatively quickly. Sure you will have some interesting dates, but if you just have attitude that you are going to have fun meeting people and practice your dating skills it shouldn't leave you bitter or frustrated.

Commit to change means to work on your presentation. You have to put the effort into your appearance again. You will see your confidence come back.

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Keith Ouellette


My background has enabled me to answer any dating questions. My knowledge in attraction, understanding interpersonal communication, and the general dating dynamics is is unmatched.


My book 200 Dates should be coming out later this year. It chronicles an unbelievable year where I went on 200 dates.


Bachelor's Degree from the University of Massachusetts, Amherst Master's Degree from the University of Nevada, Las Vegas

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