Ask Lisa: Younger Woman Insecure with Older Man

I am a 23 year old single mother. I just started dating an older guy. He is 32 years of age. I am feeling very insecure all of a sudden in this relationship. I never had this problem before. I do not know if it is because I feel like i don’t have a lot to offer this guy. I am now a single mother as I mentioned and this limits me financially, etc…  I keep asking myself why this great guy would love me? Is this normal?

I also want to mention that he has a female friend who he was friends with for many years. Right before he met me she got a divorce from her husband and they talked about starting a relationship. She is a very attractive older woman more his age and more financially stable with no children. This makes me extremely insecure. I can’t see why he pursued me over her. They are not talking anymore and he tells me that they are no longer even friends – but I have a fear that he will end up leaving me for her.

Is it common for younger women to feel insecure when it comes to older men? I really just get insecure when it comes to older women in his life. I feel like they have more to offer and he might see more in them than me. He always tells me how happy he is and loves me but I still am having trouble. I do not know what to do and I do not want to become that jealous woman. I do not want to ruin things for this relationship. If you can give me any advice I would greatly appreciate it.

Lisa’s thoughts…

Age is only a number considering the vast differences in maturity levels of men and women at various ages.  Though “age” may be part of the issue for you,  I can’t help but wonder if it’s more about your feelings about what you have to offer as a woman and possible insecurities around that.  It sounds as though his words are in alignment with his actions as well – a good sign.  So what causes you to get stuck?

Rather than focusing on the negative and things you perceive to be deficiencies compared to the other women, what would it be like to shift your attention to what you do have?  Work on keeping your insecurities in check – unless you have valid reasons for concern.  Otherwise, you might inadvertently push him away.  Explore what it is about you that might lead you to worry you’re not good enough.  Why would this “great guy” not love you?  Are there clues in your history that might uncover a tendency for self-doubt?

Is it truly about age or do you have other vulnerabilities in how you see yourself that might benefit from some exploration? Attraction and partnership are about personality matches, connection, friendship, trust, emotional safety and so much more.  And remember – he is with you.


Need advice?  Consider a Relationship Consultation for guidance.

Lisa Brookes Kift, MFT

Lisa Brookes Kift, MFT

Lisa Brookes Kift, MFT is the creator of with emotional and relationship health articles, guides, courses and other tools for individuals and couples. She is a frequent consultant for the media having appeared in,, and others. Lisa has a private practice in Marin County, CA and offers Emotional Health and Relationship Consultations via email, phone or video conference.