Where should I take a 27 year old single mom for a first date?

More information is needed.

06-13-39-40-54 / 03

Hello Diner. Congratulations on your first date. Unfortunately, you have not supplied this Fortune Cookie with enough about this woman to suggest an activity that will suit you both. I’ve known four single mothers in their twenties. Aside from their wanting time away from their kids to interact with someone as an available adult, they would all have different preferences for a first meeting.


So please help me understand her a little better. Finding this personal information via text or phone would feel at best, stilted, at worst, like an interrogation. I recommend a casual walk somewhere calming and contemplative so your date will feel at ease opening up with her interests and opinions. Look for places that are public, but are relatively quiet so you will not miss details.

Since you are looking for a first date idea, focus on activities that are interactive or relaxing–that is, activities you can do together. The key is to not make it feel like a cross-examination. Try general questions first such as her thoughts on religion, her approach to relationships, stance on social policies, and life goals. Ask about her child. In a pinch, inquire about her taste in movies, TV shows, and books. The idea is to not make it seem like you’re only fact-finding for where to take her on your first date; you’re hiding it among other questions about her interests. Be sure not to seem too eager about any of this information–it will let on your intentions of getting ideas for the outing.

If you aren’t able to learn of all her favorite activities in this go-around, don’t panic. Remember that you are playing the long game, and patience will win out. Before you part ways, arrange to meet again at a different location (to keep her guessing), and try the approach again. This time try new topics of conversation to camouflage asking for first date ideas.

Once you’ve collected that intelligence, you should realize that where to go isn’t the focus of the date. The important question, rather, is who your date is. Good luck, and I hope good things come for you two.