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Terri Benincasa
Boomer Expert ... Business and Personal Coaching

Terri is Founder & CEO of Benincasa & Associates, Inc. a unique Transitions Coaching company offering both Personal and Business services with a specialty in all things Boomer. She is known nationally as a Boomer Expert, and is a proud Boomer herself.

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6 Tips For Better Boomer Dating

For many...or most... of us, the last time we dated was in college... and now that we're single once again after decades of marriage, we are finding ourselves trepidatious about being back on the "dating scene" (to put it kindly - for some Boomers I coach, feelings range from distraught at the thought of having to date again, to a "why bother - nothing's going to come of it anyway" sense of futility before they even start...).

So here's some tips for making the experience more enjoyable, and safe.

  1. We date in the hope of finding someone who holds the same basic values and interests as our own. So make this goal your primary focus right up-front. Get a handle on what your date really likes to do and her/his fundamental values in life, then you'll know right away if this is someone to go out with again…and again… You don't want your first date or pre-dating experience to sound more like an interview, but subtly, it sort of is. Learn the right questions to ask, and the right way to ask them so you don't sound like Joe Friday, but you do get this basic information in the beginning.
  2. You'll only set yourself up for chronic disappointment if you lie or even “stretch the truth” about who you are – age, body size, still having children at home, etc. are the most common things many people try to hide initially, thinking erroneously that “once my date actually meets me, it will make a big difference…” It does indeed make a big difference – your date will be immediately turned off and you won't see him/her again. This goes back to tip #1 – you want someone who shares your values and interests, which you won't find by lying.
  3. This experience is called “dating” rather than “let's rent a UHaul!” for a reason – it gives us a chance to meet new/different people and give ourselves the time to find Mr. or Ms. Right. Back to the job-search analogy in tip #1, only very desperate people take the first job that comes along – those who make thoughtful career moves search until they find the right match for all their work-place criteria. Finding someone who is a possible mate is no different. So enjoy the dating – it's fun, it allows you to have lots of new experiences, and most importantly it's the best, no it's the only way to make the right choice that won't lead to divorce #?
  4. Your first date is just a “getting to know you” moment, so do yourself a favor and place no more of an expectation on it than that. Meet for just a drink/coffee rather than making plans for an entire evening – that way if after the first 15 minutes either of you are looking for an exit through the bathroom window, you won't have to sit through more than the cocktail or coffee in front of you. If you don't feel comfortable having no reason other than “thanks for the drink & gotta go now…” for ending the date, plan preliminary dates at a time that you truly have things you must do afterward – for example on a work night so you can honestly say “I better get home to prepare for work tomorrow…” On the up-side, if you both find yourselves enjoying the time together, you can certainly stay for more or make plans for date #2!
  5. Whether you choose internet dating or finding someone through your church or social group, keep your personal contact information to yourself until you've been able to determine a prospective date's stability. There are many services that provide a free or low cost phone number and email address that you can give people you don't know well yet. Do not be one of the many who find themselves being harassed at home, on their cell, by email, or at work because they gave someone they hardly knew their personal contact information thinking there'd be no harm in it.
  6. Take your time and do not feel pressured to jump into bed on the first date – or the third, or until you're married if that's your preference. Moving too quickly to the next level is the death knell for a quality experience: if you find you're with the wrong person, it makes getting out of it much messier & difficult; if you're truly with the right person, you make having sex more important than having a deep friendship along with your lover relationship, which can set you up for trouble later on. For most of us, feeling that initial attraction and acting on it right away is what got us into the failed relationships that have led us to the dating scene now. Don't keep making the same mistake.


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