Ask Wendy Week 1 – September 6, 2018

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From Sleepless in Newport Beach, CA:

Hi Wendy –

I’m Tina and a few years ago I lost the love of life and my very best friend. My husband Tim. We were only married 9 years (my second act) and it was so insanely amazing.

NOW, I thought it was time to date, so off I went signing up with Bumble.  OH MY GAWD Wendy!!!!!  What a nightmare.

My question is, have you tried dating sights and is there one that you think works fairly well? I’m 54….run an excellent small business.  I workout daily, have grown kids….. pretty much no baggage except for possibly a broken heart.

Sleepless in Newport Beach, CA

Wendy Says:

Hi Tina –

I am so sorry for the loss of you best friend and husband Tim. I am so glad you are putting yourself out there to find love again.  I feel your pain with the dating sites. They can be exhausting.

I have found that the dating sites that work best are the ones that you have to put more effort into to set up a profile, like  The swipe sites are much easier to set up so you tend to get more people that aren’t as serious in finding something real. I’d suggest putting yourself on more than one site. If you do want a swipe site, I like Bumble the best. I tend to get the best results. Make sure to  keep your profile positive and definitely touch on your excellent business, that you like to work out, and that your kids are grown and you have time to spend with someone, and what you are looking for. If you don’t get a response DO NOT take it personally. Remember that you haven’t met this guy yet and you have no idea what is going on in his life at the time that might prevent him from following through. The dating sites are tough and can be frustrating,  but they definitely do work. Don’t delete those sites just yet.

Stay positive and when you least expect it…


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From Game Player:

Hi Wendy –

Here’s a little history before I ask you my question:
I was in a long-term relationship right out of college with whom I thought was the love of my life, for 12+ years – we never married mostly because I didn’t think it was important. (Goldie Hawn was my idol at the time and she and Kurt Russel never tied the knot either).

He wound up falling in love with one of our friends (his colleague) and did a serious number on my heart.

For a long time, nine years to be exact, I never allowed myself to get serious with anyone. I went on quite a few dates and really had no issues meeting men. It was during this period of my life that I experienced the hunting nature of men. The more I told the men that I dated that I didn’t want anything serious, the more they pursued me. There were a few that didn’t, but the majority of them did. The less available I was or the more I blew them off, the more they would chase me.

My girlfriends and I would often ponder this phenomenon and conclude that it has something to do with the chase and how many men (and women) want what they can’t have.

So now that I feel ready to start anew and could be ready for some steady male companionship once again, I am wondering if I need to play this cat and mouse game. I’m too old for games, really, and I would like to live a genuine, honest life, but in the beginning of a relationship, do some games need to be played in order to get the attention and keep the attention of a man that I might be interested in pursuing?

Game Player

Wendy Says:

Hi Game Player –

Unfortunately, people tend to want what they can’t have. It’s human nature. So, of course someone who is unavailable is seen as more desirable. I would say what makes someone the most desirable is having confidence in themselves and having a full life. Not needing, but wanting to share your life with someone is very appealing. So should you play hard to get? I’d say no.  That could backfire if the other person thinks that you are not looking for something serious or that you do not have time or are not making enough time for them. I think you should just live your life. Make plans with your friends. Pursue  your  passions and hobbies.  If you do meet someone you are interested in, don’t rearrange your life for this person but do make some time. Include them in something you are already doing. For instance, if he asks you out for Tuesday and you already have signed up for a yoga class, don’t cancel your class but instead invite him along. If you already have plans that you cannot or do not want to include him in, just let him know that you already have plans and suggest another night or to meet up with him after your plans. I would also recommend that you let him be the one to pursue you. Men like to be the hunter. Let him be the one to ask you out and text you in the beginning. Let him wonder a little (ok maybe that’s a little bit of game playing- but it works).  You never want to appear too eager or too needy. I wish you luck on your hunt. Or should I say, his hunt…


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From First Date Kiss:

Hi Wendy –

I’m curious about one thing. How do you give a man a kiss on the cheek to thank him for a lovely time after a first date? I have tried this a few times and each time, the man gets the wrong idea and goes in for a big tongue kiss. Then I wind up feeling like a fool. Can women cheek kiss anymore?

First Date Kiss

Wendy Says:

Hi First Date Kiss –

This actually happened to me recently. After an “eh” date, I knew I didn’t want to kiss him. When we were saying good-bye he tried to kiss me.  I turned my head so he would kiss my cheek instead,  but somehow he managed to kiss me anyway, tongue and all.  I’m still not sure how it happened. Normally, a man  is not going to kiss you if he doesn’t feel confident that you are going to kiss him back, but there are always a few that will try anyway. You can try to lessen the chances of that happening.  There is no need for a kiss on the cheek to thank him. I think a good-bye hug is nice. Don’t stand so close when you are saying good-bye. Turn your head away as you lean in for a quick hug to say thank you. Do not linger with small talk. Hop in your car and be on your way. Hopefully on your next date you will want the kiss, and it seems that you know how to get it.  😉


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From Shqyna:

Hi Wendy –

I have been trying to navigate the online dating world after losing my husband more than 10 years ago – I can’t seem to get it right. Any suggestions on choosing someone who isn’t untruthful?


Wendy Says:

Hi Shqyna –

Thank you for writing.  I am so sorry for your loss. I am glad to see that you are putting yourself out there again to meet someone.  Unfortunately, there are a lot of liars online (and in the real world). The best advice I can give you from my experience is to read between the lines, in a profile and in person. First, look at the pictures carefully. You can usually tell if the pictures are more than a few years old by what they are wearing or hair styles or even a date stamp in the corner. Be wary if there is only one picture posted. It is hard to tell what someone looks like from just one picture. People can tell you whatever they want, but they will always show you who they really are if you just pay attention. Carefully read what people are writing.  If they have a 25 year old daughter, chances are they aren’t 45 and are probably older. If their profile lists more things they “aren’t looking for” than things they “are looking for” then to me, they sound bitter and angry and probably aren’t ready to be in a relationship. The more information that is put into a profile means they took more time to fill out the profile, and they are probably more serious about meeting someone. Make sure you are clear about what you are looking for.  If you are looking for an exclusive relationship, then make sure to say that. Ask to have a phone conversation before you meet. Ask questions and really listen to what they are saying and how they are responding. If what they are saying doesn’t add up then walk away. If it seems too good to be true, it probably is. Everyone online is trying to sell themselves, so there will always be a little bit of a stretch in the truth.  With that being said, there are plenty of great guys online. Try not to have too many dealbreakers and go into the process with an open mind. Make the first meeting short and sweet, coffee or a quick drink. Think of it as an initial meeting and not as a date, so if it doesn’t work out you won’t be so disappointed. Save dinner for a second date when you know you want to spend more time with this person. Try not to become discouraged. You never know..that next first date could be your last first date.


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About Author

Wendy works as a marketing analyst for a commercial real estate firm. She is a divorced mom of two teenage daughters, who is soon to be an empty nester as her younger daughter goes off to college. After sharing all of her crazy dating experiences with her friends over the years, they have finally convinced her to write them down and share them with the world. Wendy believes one day she will find her perfect match and is enjoying the crazy ride until then.

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