Wayne and Wanda: I’m dating a great guy, but my history is making me insecure

Dear Wayne and Wanda,

I’m in my mid-30s and have had a few long, serious relationships but have never married. I’ve also never had kids, and I’ve maintained a busy and active social life. I guess my love of fine dining, live music, and a stint working at a bar in my early 20s is to credit for the fact that the majority of my friends work in the service industry.

This is a fun friend group for sure, though admittedly, I don’t socially surround myself with “adulting” types. That’s probably why my three previous serious relationships bordered on dramatic, maybe even a little dysfunctional. There was a lot of drama, bad communication, fighting, lies, etc. Two of them were unfaithful to me (which ended those relationships). In all three relationships, I felt like the responsible one — and I use that word lightly, meaning I was kind of delivering the bare minimum, like the fact that I had health insurance, a steady paycheck, and a dog.

Now I find myself in a whole new place, dating a new guy. He is the most mature adult I’ve ever dated. He owns a house and has an incredible job that required years of school. He volunteers for several nonprofits, sits on a board of directors, and regularly goes to church. He knows how to cook and he’s always coming up with creative date ideas — all my past boyfriends wanted to do was go to the bar and maybe split a basket of tater tots.

I’m freaking out because frankly I just feel unworthy of him. I worry he’ll realize he’s picked someone who can’t match his emotional maturity and drop me. I worry I can’t keep up — he feels too good to be true. I’m afraid his friends (all equally mature and impressive) will think my friends are losers and lushes. And I really, really like him, so all these fears are compounded by that. I know I need to relax or I’m going to self-sabotage this but I can’t seem to just relax and enjoy this. Advice?

Wanda says:

First thing first: Congratulations on finally breaking out of the dysfunction cycle that characterized your previous dating history. You describe stressful and unhealthy relationships that perhaps in the moment were misunderstood as passionate, intense or exciting, but were actually really, really bad for you. No one needs to be lied to, cheated on or otherwise mistreated, and it’s all too easy to connect emotionally to someone who needs help, and feel self-worth in being the one who can support and fix them.


Unfortunately, your time with these past paramours has seriously screwed with your self-esteem and sense of worth. Rather than focusing on what you bring to the table, you’re framing your value as a partner by homing in on unfortunately negative previous patterns that left you feeling less than fabulous. And this is messing with your mind at a time when you should be kicking back and basking in the honeymoon phase of your new relationship.

You’ve now picked this guy and are falling hard for him; well, good news, he has picked you too! And that’s surely because of the wonderful traits he sees in you — not because of what you perceive yourself to be lacking. Can you be happy in a relationship where there’s honesty, open communication, kept commitments and actual date nights? I promise you, you can.

Wayne says:

Those aren’t fears — they’re insecurities, likely mixed with a dose of early-dating anxiety. I think you’re underselling and undermining yourself. So allow me to flip this scenario and then tell us how you feel …

What if your new guy is freaking out, fearing his routine is so boring and he’s waiting for this exciting social butterfly he’s lucky enough to be dating to finally see that? What if he watches you in your element, as the center of attention for so many fun friends, and is worried he won’t fit in with the cool kids? What if your life and relationship experiences have given you a sense of emotional maturity that he admires? And what if his friends see you as bold and impressive, and they know that their friend is the one who scored big time?

I don’t have to guess on this one. He really, really likes you too, and I bet he finds that you two and your lives complement each other so well. So yes, you do need to relax or stop with the self-sabotage. It’s your confidence and personality that likely landed him. Keep rolling with that and have fun with this great new situation.

[Wayne and Wanda: I’m dating a woman who says I’m not her ‘type’]

[Ask Amy: My boyfriend doesn’t want to hang out with me]

[Dear Annie: I’m not happy with where my spouse’s career has taken us]

[Wayne and Wanda: My fiance is in debt, and we can’t agree on how to move forward financially]

Wayne and Wanda

Wanda is a wise person who has loved, lost and been to therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at