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35 Tips for Middle-Aged Men Returning to the Dating Scene


This post is intended to help the middle-aged guy who is just getting reacquainted with the dating scene. If you are starting out again, fresh on the dating scene after being married and subsequently divorced, these will help you. I have compiled this list of tips from my past year-and-a-half of experience back on the dating scene.  The order these are listed in is no indication of rank or importance.

  1. Resorting to online-dating sites like Match.com or eHarmony.com does not indicate failure on your part.  These sites are a great way to meet like-minded women with equally busy lifestyles.
  2. Start an exercise regiment – getting toned and healthy will improve your self-confidence and overall health.
  3. Quit smoking.  The vast majority of women I have encountered highly-disapprove of smoking.  It can flat out kill your chances with many women.
  4. Keep your bachelor-pad clean.
  5. If you’re losing your hair, don’t try to hide it.  Keep your hair short and neat or shave it all off – embrace it, don’t try to replace it.
  6. Trim your damned nose-hair… often.
  7. Trim or pluck out ear-hair… very often.
  8. Always wear deodorant.
  9. Wear a masculine cologne, but do not bathe in it…
  10. If you are wearing shorts, lose the tube-socks.  White socks (when worn with shorts) should not extend above your ankles.
  11. Wear clean, decent-looking (not all-white) gym shoes when wearing shorts.  The ankle socks with clean gym shoes will give you a more sporty, youthful appearance.
  12. Wear clothes that fit you.  I personally prefer athletic-fitting shirts.  I used to wear XL-sized shirts because they were more comfortable and made my small/thin frame appear larger…  A good fit,  will get you more mileage than expensive clothing.  I now wear only L-sized shirts that are the right size for me and accentuate my newly-toned arms.
  13. A study has indicated that women find a man’s arms to be his most sexy, attractive feature.  Thank goodness, because I hate working out my abs.
  14. Eat right… Cut down on fat and increase your fruit and vegetable intake.
  15. Stay tuned-in to topics that interest women…  You don’t have to become an emasculated, metro-sexual, but women enjoy conversation.
  16. Be confident.  Know who you are and be comfortable with that.  Women are drawn to confidence.
  17. Be a leader.  You can lead with women without being a chauvinistic, arrogant asshole.
  18. Do not compromise your beliefs for anyone (unless your beliefs are totally screwed up of course).
  19. Be organized.
  20. Keep your car clean inside and out.  If you know you are going to have a woman in your car, you’ll want to get rid of the McDonald’s bags, and vacuum it out.
  21. Be consistent, but not predictable.  Women like stability as well as variety and mystery – act accordingly.  Mix it up, but do not freak them out.
  22. Treat women with respect, but be sexual with them (not creepy).  You will build their attraction towards you.
  23. Many women on the dating scene at this age are divorced, single-mothers.  Understand that her kids SHOULD be priority over you.  If they aren’t, there’s something wrong with her.
  24. NEVER ignore RED FLAGS!  Some women are no good at all…   Be familiar with personality disorders such as Narcissistic Personality Disorder and Borderline Personality Disorder.  Learn what to watch out for and what to avoid.
  25. Deodorant can be used on and around other areas of your body – use your imagination as to why this may be helpful to you.
  26. Grooming can be done in areas aside from your head – use your imagination as to why this may be helpful to you.
  27. Shave.  The odds are in your favor if you do.
  28. Learn to iron and use your iron.
  29. Learn to listen…  Pay attention to details and remember them.  If you want to really light her up, bring up a small detail she mentioned on a prior date.  You will be reinforcing the idea that you listen and care (even if you really could care less).
  30. Do not use or take advantage of anyone.  Karma IS a real bitch…
  31. Keep tight-lipped about prior relationships and their details.  She make act like she wants to know, but she really doesn’t want to know.  Trust me.
  32. Be chivalrous, but don’t kiss her ass.  Hold doors, let her order first, etc…
  33. DO NOT PAY FOR EVERYTHING.  Make her INVEST in you too.  She is not a queen, and you are not her subject.
  34. Keep your options open and do not spend every moment you’re available with her.  Remember your interests and friends.  Be sure to value time to yourself.
  35. Have firm boundaries.  Stand up for yourself.  You will be tested from time-to-time.  Always be willing to walk away from a bad or unfair deal.

Guys (and gals), if you have more tips, I’d love to hear them.  Please post yours in the comments section below…

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3 comments to 35 Tips for Middle-Aged Men Returning to the Dating Scene

  • Ouch ouch on number 24. I know you have your reasons for saying that, but it appears a tad harsh.

  • Dan (OmniSwami.com)

    Hi Rose,

    I hope you can understand my perspective… I had NO idea what I was getting into with my exgf. I had NO prior knowledge of BPD. She left me in tatters; I was at an utter loss as to what happened.

    The “no good at all” portion is a bit harsh and a bit transparent into my bias, aye? I guess I should clarify that statement and what I intended by it… My exgf was not “no good at all,” in fact, she was a beautiful person much of the time. Unfortunately, from the perspective of dating and relationships, she wasn’t at all capable of reciprocating love in a reasonable way.

    That being said, I do have to remember those in your situation as well, and I truly mean you no disrespect.

  • I realize that you mean me no disrespect.

    I had NO prior knowledge of BPD either when my daughter was diagnosed with it only three months ago. BPD all very new to me as well.

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