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

Rachel Dack
Rachel Dack Updated:
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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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