Angela, eight months ago, a guy I was falling for harshly dumped me.  After a few written apologies, we have started seeing each other again.  I am thrilled to have him back in my life, but worried I may end up heartbroken…again. Right now our relationship is better than the first time we were together. His intentions feel far more sincere, but I am unsure how to address my lingering concerns.  Any help? -- Ex Factor

Fool me once, shame on me; fool me twice…when then he really is a jerk, right?  Or maybe you’re worrying YOU will be the jerk if he breaks your heart again.  Doubting his intentions after being dumped (harshly, no less) certainly is a normal reaction. The question is, how do you move on from it?  You can either keep feeling uneasy about the past, which will definitely add strain to your relationship and likely manifest itself in another breakup, or you meet him back at start.  If you want it to work this time, you must do the latter. Let go of what happened previously and only see the present state of the relationship, opting to let the past be the past.  Take it one day at a time and don’t get ahead of yourself. Gradually, your trust will come back.
Good luck.

Angela, I’ve recently met a wonderful, intelligent, beautiful, hilarious woman, but there is a problem.  She is significantly younger than I am.  (Don’t worry, it’s legal.) My children are raising their eyebrows.  How do I address the stereotypical stigmas attached to dating out of your age range? -- Gregg

Gregg, It sounds like you have met someone amazing.  There’s a great quote a friend always says: “If you have to explain it, there’s a problem.”  No need to explain or justify who or why you are attracted to someone.  If it works for you, then it works for you. Period.  No mater how much energy you waste trying to tell others what a perfect fit you two are, they will have their own conclusions.  Let them talk. You’re the one with the hot young girlfriend, and well, they aren’t. Jealous much?

Now let’s address the subject of your children’s approval.  From the time they are teenagers through adults, our children pretty much disapprove of something we do on a daily basis.  When it comes to their parents dating habits, they are merciless. (It’s a bylaw in the offspring code of conduct.) Even if Prince Charming rode up to my front door, my son would give a disapproving look and say, “Whatevs, Showoff!” Your kids will either come around or they won’t.  It’s out of your control.  

As for the constant ribbing you will receive from your friends, just remind them that you are the only one that actually doesn’t need Viagra anymore.  

I’ve been dating the love of my life for the past five years.  We have a dog, apartment, stable careers, supportive family and friends—the works.  But there is one think I don’t have and it’s missing from my left hand.  Marriage was an exciting discussion a year ago, but has not been brought up since.  Now I am feeling insecure and unsure.  What do I do?  -- Always the Bridesmaid

Dear Bridesmaid,  As harsh as this may sound, why would he want to get married? You’ve created the perfect relationship scenario without him ever having to make a serious commitment.  There is no incentive for him to change anything about your status.  In his mind, life is great. Why would he risk upsetting the apple cart with marriage?

The answer to that is: Because he will lose you if he doesn’t.  No ultimatums, temper tantrums, or tears involved, you’ll need to have a conversation.  Pick a weekend afternoon when things are stable and you are relaxing at home.  Without being emotional, tell him, “relationships are like sharks; they move forward or they die.” (I love that line.) It’s time that you move forward.  You love him, and know he is the one you want to spend your life with, but if he doesn’t feel the same way, then it’s time you started to think about your future differently. Give notice that at the end of the year, which gives him a solid six months, you will be moving out and starting a new chapter of your life without him.

That’s the easy part.  The hard part is going to be sticking to it.  If your talk doesn’t have him running to Tiffany & Co quickly, start making little moves that indicate you are serious, like researching a new place to live. If December comes and your beau has not put a ring on it, my dear, it really is time for that new chapter. Don’t feel insecure. The environment that was created gave him the perfect commitment-phobe arrangement.  You just have to shake things up a bit.  My guess is that he will come around.

Have questions for Angela?

Send your dating queries to kevin@bocamag.com.

About Angela Lutin:

Angela Lutin has won the adoration and loyalty of her riders at Flywheel Sports in Boca, where she has emerged as the most sought-after indoor cycling instructor in South Florida. In her spare time, the divorced single mom has launched a popular dating blog—essentiallyangela.com—on which she dispenses musings on life, navigating the singles scene and much more. Angela will answer your dating questions every Thursday at bocamag.com on her “The Naked Truth” blog, which she is doing exclusively for Boca Raton magazine. “A chef is the expert on food, a stylist knows the right clothes,” she says. “And me? I’m the one you come to for questions about love, sex, and relationships. I’m certainly experimenting to find the right formula every day.”