She’s Always with Friends. How Do I Ask Her Out?

Rachel Dack

Written by: Rachel Dack

Rachel Dack

Rachel Dack is a licensed clinical professional counselor (LCPC) and relationship coach specializing in individual and couples psychotherapy. Rachel's areas of expertise include relationships, dating, mindfulness, anxiety, depression and self-esteem.

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Reader Question:

I have been flirting with a younger girl. She said she needs a “real man” and her present boyfriend is an “immature child.”

We have talked but she is very immature socially. She also is always with her friends and never alone.

How do I go about asking her out?

-Todd (Pennsylvania)

Rachel Dack’s Answer:

Hey Todd,

I admire you for wanting to go after someone you are attracted to. However, are you sure asking her out is the best move while she has a boyfriend?

Although I am not sure how serious her current relationship is or how much she is invested in her current boyfriend, it is not a good idea to start a new relationship while either of you are in a relationship.

It can lead to cheating, dishonesty and hurt for all parties involved.

I recommend spending more time with her if you would like to while being respectful of her relationship. If she badmouths her boyfriend, you can ask her if she is truly happy with him or why she is staying with him if she finds him to be immature and not fulfilling for her.

You also could let her know you are interested. However, I would be cautious in getting too involved with her until she is single and moved on from her current relationship so you don’t get hurt.

In the meantime, get to know other women and be open to connecting with someone who is single and emotionally available to you.

Take care,


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