Widows Wear Stilettos

Q: What’s the number one message you hope will resonate with singles who read your book "Widows Wear Stilettos: A Practical and Emotional Guide for the Young Widow”

The prevalent message is that there is indeed life after loss and that albeit different from the life that you may have envisioned, it can again be a fantastic life.  Grief deserves one's time and attention; however it does not deserve the power to take over a life.  Too many people permit this to happen and Widows Wear Stilettos is dedicated to helping people get proactive about healing; rather than permitting grief to take over and eventually permeate their lives.

Q: How can you know if/when you are ready to date after a loss?

There are several excellent ways to know if you are ready to begin dating after loss; be it by loss, divorce or breakup:

You Have "Reclaimed" You
Whether by loss, divorce or breakup, immediately following the loss of a relationship is not the time to jump headlong back into dating.  Prior to the resumption of dating, you must first recover from your prior loss and you cannot accomplish that in a “hurry-up” fashion.  You must take the time and patience to sufficiently recover from the trauma that you have experienced and get to know yourself as a “single”.

You Realize That You are “Not Guilty”
When you have been functioning in life as one-half of a couple, you become “conditioned” to thinking of yourself in those terms.  All of sudden, you are no longer one-half of “The-Two-Of-You"; yet your emotional being is still in the “one-half of a couple” mindset.  When you find yourself attracted to someone or you make a decision to resume dating, you may feel guilty - as if you are actually “cheating” on an ex or on a late spouse.

While guilt is a perfectly normal emotion to encounter during any healing process, it can nonetheless hold you back from the resumption of dating.  Realizing and accepting that there is no reason whatsoever to feel guilty about dating and / or seeking companionship is a necessary step in the knowledge that you are ready re-enter the world of dating. You are entitled to a life of abundance and happiness and companionship and love are part of that entitlement. 

The Absence of Anger
It is absolutely normal to feel angry at whatever circumstances ended the previous relationship.  Sadly, many choose to stay “in the angry” or “in the bitter” to the point that they are unable to move forward with their lives.  These same people may take this anger out on prospective dates as well.  The resolution of anger is an important step toward preparing for dating again.  When you have made peace with the circumstances that ended your prior relationship and you have begun to move forward from that loss, you are truly ready to begin exploring the world of dating again.

Are You Happy On Your Own?
Are you content with yourself as a “single”, on your own without the necessity of the presence of another person?  Do you have your own career, your own hobbies, your own pursuits, your own set of friends with whom you play sports, dine or hang out?  When you are content with yourself as a single person, you are genuinely ready to begin the dating process again, because you are not simply “filling the void” that your last partner left. 

The companion element to being happy on your own is the ability to go out alone and enjoy yourself.  Have you been out for a meal on your own?  How about a movie or a comedy club?  As a society, we are accustomed to either traveling in packs or with a spouse / significant other; however, you must be happy and content with your own company.  This contentment will enable you to make wise decisions in your dating choices and when you do invite companionship into your life, it will be for all of the right reasons.

Are You “Emotionally Available”?
Your emotional availability will have everything to do with (a) the amount of time that you have spent recovering from your prior relationship and (b) your willingness to make yourself emotionally available.  Years ago, I once dated a man who had not recovered from being broken up with in high school – thirty years earlier.  This gentleman made a conscious decision not to make himself emotionally available to anyone else because of one prior bad experience that took place decades earlier. 

Ask yourself if you are truly ready for the dating experience, and if you are capable of making yourself emotionally available to another.  If you don’t feel quite ready yet, stop and take more time for you – it's OK to do that.

Q: What are some of the biggest dating challenges suddenly singles face and how can they overcome those obstacles?

The most common lament is, "There are no good men / women" out there", which of course could not be farther from the truth.  The response that I always give in turn is, "What have you done to try and find these 'good' men / women?"  Most people either haven't truly made a sincere effort to find someone (and no matter how wonderful you are, people are not going to line up outside your front door waiting to meet you) or they have one or two bad dates and unilaterally decide that all men / women are "jerks". 

Rather than complaining, choose to instead take control, get proactive by deciding that you are ready to meet someone fabulous – and then get out there. Let your friends know that you're open to dating, investigate online dating sites, get out of your house (for other than work and grocery store runs) and engage in your favorite hobby or pastime…people are everywhere. 

The other challenge is the invisible "list" that many have in their heads of the "perfect" man / woman.  While I believe that being alone is preferable to "settling" for someone who is not right for you, when you get rid of the "list" (i.e., must be a specific height, weight, hair color, body type, drive a certain car, etc.) and keep an open mind and an open heart, you will dramatically increase the number of dates that you have – and the chances for relationship success as well. 

Always remember that the right person is looking for you just as hard as you are looking for them. Will you have bad dates?  Absolutely.  Will you at times get discouraged?  Definitely.  However, do not ever give up…think about what  you could be missing if you decide to quit dating based on a couple of unfortunate experiences. 

Q: Understandably, many suddenly singles/widows have a fear of dating. What advice would you give to help them get over the anxiety they may be experiencing?

Oftentimes, it's not a "fear of dating", per se; but rather what may come as a direct result of dating. The "fear of dating" may actually be underlying fear(s) instead – the fear of experiencing another loss, the fear of intimacy, a fear of vulnerability or the fear of being hurt again.  It could be the “last ten pounds” that you think is holding you back.

It's important to honestly assess what exactly it is that is causing the fear.  Once you have isolated, identified, addressed and moved forward from whatever it is that you feel might be preventing you from dating again, you will then be able to enthusiastically jump into the dating world in a positive way.  Again, it's vital not to base a future on the experiences of the past.

(P.S…no one cares about the “last ten pounds”).

Q: If you are thrust back into the dating scene after a loss, it’s a lot more challenging to keep a positive self-esteem. How can individuals keep confidence levels high so that self-doubt does not interfere with their love life?

Everyone's self-esteem has taken a hit at one time or another; particularly if the last relationship ended because someone cheated or otherwise behaved dishonestly.  We tend to think in terms of "What was wrong with me" as opposed to what is wrong with them.  For those who experienced the loss of a partner, self-esteem can still be an issue – the "he/she's not around to care about me so why should I care about myself" mindset is quite common.

Regaining confidence comes from within and it takes committing to yourself to get that confidence back. It's a fact that you will gravitate toward on that which you choose to focus and if you focus on you in a positive way as much as possible, self-doubt cannot thrive.  Start by treating yourself the way you deserve to be treated; both inside and out. Get around the people in your life who are going to support and reinforce you as you begin to move forward.  Lastly, don't use your past experiences as a barrier against the potential that your future holds…in other words, don't hold the experiences of the past against the people who are in your future. 

Q: Comparing potential prospects to a past love is common but can be detrimental during the dating process. Any advice you can give on this topic?

We tend to have “selective amnesia” when it comes to our previous relationships; remembering only the good - the good times that we had and the wonderful memories that we’ll have always.  That’s fine – but don’t hold up a memory as a “yardstick” against which you are measuring prospective dates - they will not be able to compete.  It’s unfair to start sentences with, “Joe always used to….” or “Susie would never have …”, because absolutely nobody “always” did this or “never” did that.  Everyone deserves to be judged as an individual, on their own merits and should not be compared to anyone in your past.  By all means, honor, keep and treasure all of the wonderful memories that you have; however, you need to be able to put the Ghost of Relationship Past in its proper place in order to enjoy someone new. 

Q: What are some taboo topics to avoid in the getting to know you phase of a relationship?

While most (if not all) of the following subjects can and should be discussed as a relationship progresses, they are definitely taboo" on the first date and during the infancy of a relationship:

Personal finances; yours or theirs:  Talking about the current state of the nation or world economy is fine; talking about your own personal financial situation or inquiring after your date's financial state of affairs is not.  In fact, I usually advise that until an exclusive relationship is established, finances are to be kept private. 

Overtly sexual discussions or topics:  Playful flirting is fun and certainly part of the dating process – who wouldn't want to be told that they look fantastic or that they have a great personality.  However, imagine my own chagrin when a simultaneous "first / last date" started describing one of his sexual predilections, in explicit detail and approximately ten minutes into the date. 

What "message" do you want to send your date…and what messages do you want your date sending you.  Unless you and / or they are interested only in the dreaded "booty call", steer clear of sexual discussions for at least the first few dates.

Graphic / specific details as to how your last relationship ended:  While I absolutely believe that discussing experiences with exes or late spouses is acceptable (after all, most of us have one or the other and it gives a "glimpse" into how we got to where we are now), don't go into a great amount of detail at the beginnings of a relationship – you can easily come off as angry, bitter or if your relationship ended as a result of loss, still going through a grief process.  Discussing past partners too soon, especially with great passion (anger, sadness, tears, etc.) will give the impression that you are not yet ready to date. 

Illnesses / Ailments / Family Issues:  If you or a loved one has overcome a serious illness or disorder, that's wonderful.  However, it can be off-putting to go into great detail about illness, treatments, addictions or recovery challenges too soon. The same rule applies to any kind of family issues (i.e., custody or estate battles, estrangements from relatives, an unfortunate childhood, etc.).

Job / career difficulties:  It's common and certainly fine to discuss your career(s) on a first date; it's conversation that will generally give you a great "sneak peek" into the kind of person with whom you're sitting.  However, if you are experiencing difficulties at work (a bullying boss or co-worker, a round of layoffs, etc.), keep that information to yourself while you enthusiastically talk about why you love your career.  If you aren't particularly happy in your current career, talk instead about the career to which you aspire and why. 

Politics / religion:  You can usually get a good "feel" for where another person is politically and / or religiously in general conversation; however, unless both of you are clearly on the "same side of the fence" (i.e., you met at your house of worship or at a political party fundraiser), these subjects should be approached with great caution; if at all. 

Q: First date mistakes suddenly single individuals should avoid?

Dressing too provocatively (ladies): When selecting wardrobe for a first date, ask yourself again, "What kind of message do I want to send?"  Wearing something cute and on-trend that shows you off in a flattering way will get you sincere compliments.  Wearing something that reveals too much skin will get you sincere propositions – and not in a good way.

Dressing too casually (guys):  Women appreciate nothing more than a man who knows how to dress – it shows that you care about what she thinks and the impression that you want to make.  You don't have to wear a suit to a coffee date at the beach, but nice jeans and a shirt on a movie date will be appreciated far more than shorts and flip-flops.  Use your good judgment here – women are paying attention. 

Going anywhere too "romantic": Keep the first date "light" as to destination and surroundings.  Dimly lit restaurants with candlelight, tuxedoed servers and strolling violinists are fantastic – on subsequent dates.  A romantic atmosphere is putting way too much "pressure" on both of you (not to mention on a wallet). 

Marriage / children: There's nothing wrong with wanting to get married (or remarried) and have children (or have more children).  However, this is not an appropriate discussion on a first date.  Ladies, you don't want a date feeling as though he is going to be dragged to an engagement ring store after knowing you for three days.  Guys, this may seem obvious but please don't propose on a first date – it's not cute, it's not romantic, it's just plain scary…and yes, it does happen.

Talking about yourself too much:  There should be a comfortable conversation going on – remember, "conversing" takes two people; "lecturing" takes only one.  If you feel like you're doing most of the talking, your date likely feels the same way. Segue with a smile by saying, "That's enough about me, let's talk more about you…" and then follow with a question about them.

Drinking too much: Aside from the obvious drinking-and-driving safety issues, alcohol also lowers inhibition and too much can also eliminate common sense.  You don't want to say – or do – something that you will regret the following day…and no one likes to be out with someone who is drunk.  Limit yourself to two drinks and then switch to non-alcoholic beverages.

The biggest taboo of them all: No matter how attracted you are to someone; no matter how great the date is going or how beautifully you are getting along – do not have sex on the first date; particularly if you have hopes of seeing that person again (for other than the aforementioned booty call).  Conversely, if you are with someone who is trying to pressure you into having sex after knowing them all of three hours, don't walk  - run out the door.

Q: Do you recommend online dating and if so how can individuals who have overcome a loss ease into the dating game?
If you are feeling tentative about dating in general, online dating is a good place to start.  You are far less vulnerable on a dating website than you are perched on a barstool on a Friday night, which is not the most desirable way to meet people anyway.  With online dating sites, you possess far more control of with whom you wish to communicate.  The site itself acts as a “buffer”, affording you a “comfort zone” between yourself and prospective dates. 

There are several advantages to internet dating.  You can communicate with as many or as few people as you choose, as well as how often  - or not at all.  You can move as slowly or as quickly as feels comfortable.  There is also the peace of being able to remain somewhat anonymous until such time arrives that you feel at ease with revealing more personal information. 

If you are considering online dating, keep the following very important points in mind:

1.    Remember that you are in complete control. You get to make all of the choices and can specify exactly with whom you wish to communicate – and just as vital, with whom you do not wish to communicate!

2.    Take care in selecting a dating site.  In choosing a site or sites with which to affiliate, consider the following:

a.   What is the site’s privacy policy regarding email communication?  All email should come through the site and the site should guarantee the protection of all of your personal information. 

b.   The site should have some sort of abuse-reporting department, policy or plan, as well as a way for you to immediately block communication from anyone with whom you do not wish to associate

c.  What sort of customer service department does the site provide?  Look for sites that offer several avenues of customer service contact (i.e., a toll-free telephone number, email address, even live support online).  If a site’s idea of customer service is an FAQ page, you’ll want to pass. 

3.  Don’t reveal too much in your profile, but you will want to be honest in representing yourself (particularly regarding your age).  It might be wise to have a trusted friend or even an older child read over your profile prior to posting it on a site. 

4.  Remember that your initial communication is with someone that you do not know.  When you meet someone online with whom you’d like to communicate, do so through the site for a while prior to giving out a personal email address, telephone number, last name or any other personal identifying information – in other words, take your time to get to know who it is with whom you’re corresponding.  If someone’s first email to you consists of simply asking for your phone number, or is asking you to call them right away, meet you the same day / evening or says that they are discontent with communicating by email (i.e., "I don't like to type so can I just call you"), they need to be blocked from further communication..

5.  When it comes time for that first date, always meet in a public place and make sure you tell at least one person where you are going and with whom you are meeting.  An excellent suggestion is to contact your “safety person” mid-date so that whomever you are with knows that someone somewhere is expecting you.