Ask Kiki – How Should I Wear My Hair for Dating?

As a dating coach I am often sent questions about specific love life situations that women are going through.  I have decided to post some of those here in my blog because I realize that many of YOU are going through similar issues.  I have changed the names* to protect the identities of the parties involved.  Feel free to comment below if any of these situations resonate with you.Ask Kiki banner2


Hi Kiki.  I am going through a transition with my hair (relaxed to natural) and at your seminar at Lord & Taylor you mentioned assessing what has worked well with men.  I honestly don’t know what has worked for me as there has been long periods of time where I wasn’t getting any attention at all, and some where it seemed like I was meeting a lot of men at one time.  This was before I decided to go natural so I am now clueless as what to do.  Help!


Hi Jackie,

Hair questions are common, even for men.  I was recently asked by a male client if he should go bald again.  He said that when he was bald it was harder for women to ascertain his age.  He said he looked younger and it was also harder to tell his ethnicity when he was bald.

“Why did you grow your hair back then?” I asked.

He shrugged and said that it was probably because the weather got colder.

This is the very point that I brought up at the Lord & Taylor event.  If you know that something has worked for you in the past with the opposite sex, keep using it!  This is especially the case if you changed that thing and did not get better results.

I wrote a post a few years ago on LONG HAIR VS SHORT HAIR (read it here).  I said that most men prefer their women to have longer hair because men perceive longer hair as more feminine on a woman than a shorter cut.  But if you get more attention from men when your hair is short, wear it short.  By all means evaluate what works and what doesn’t and do what works.

It may take some time.

So Jackie, since now your hair is natural, you will have to find a style that flatters you.  It is definitely OK to also grow your hair natural at home while out in public you wear pretty scarves, hats, wigs, hairpieces, weaves or anything else you like your look in.  I know of some natural women who cut their hair secretly to transition, but bought wigs the length their hair had been when relaxed and no one was the wiser.  In other words, the general population does not have to be in on your transition phase at all, if you choose to keep it secret, especially on dates.

If you do cut it off and do the big chop, you may find you love it short and feel so sexy and confident that men are flocking your way.  You can test it out with a short wig before you cut it if you haven’t already.

Do like the celebrities, try many styles and see which looks bring the men.

Which styles do you like below?  Natural or relaxed?  Long or short?







Let me know how it works out.  Send me a pic!
If you want to be married in the next two years, contact me today!
As featured in EBONY Magazine
Kiki Strickland

“Married in 2 Years or Less” Dating Coach

p: 202-718-7797 a: 1629 K St NW Suite 300 Washington, DC 20006


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