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Ask Shari: Dating with Kids, Being a “Cougar”, and 5 Best First Date Questions!

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Ask Shari: Dating with Kids, Being a “Cougar”, and 5 Best First Date Questions!

This week’s edition of Ask Shari is live! Shari Hardies, LCSW, is here again to answer your questions.

Q: Hi Shari! I love going out on dates, but I’m nervous about talking about the fact that I have young kids. I don’t want to scare off anyone, and I’m not so good at being subtle about it. Do you have any good techniques or know how and when to bring up such a subject? Thanks!

A: Hi Dating Mom, thanks for writing in and taking a moment to get some thoughts on this question, it is an important one. I really commend you for dating and enjoying the dating world as much as you do! Give yourself some props because that is no small feat in and of itself. I wonder, why do you feel that your children would scare off anyone worth dating? Have you had some negative experiences?

I have come across many people, awesome single guys that love children and may find a women with children very attractive. Regardless, I can totally understand not wanting to automatically mention your children to just anyone, after all this can be tricky. I would imagine you would want to protect yourself as well as your children, some people just don’t need to know everything about you and your home life.

The biggest question on my mind while I answer this inquiry, are you dating for fun or for a real relationship? In real life you are a Mom and a woman, this is an awesome dual role which makes you A-mazing but can also present some challenges. I would recommend that if you are dating to meet someone that you will have a long term relationship with than go ahead and bring up your children. I love that you aren’t subtle about it because children are not subtle! I would work it into small talk early on in the date, “Oh last time I was here I was with my children” or “It feels so great to be spending my time with an adult, I have small kids at home”.

I think it’s important to work your children into the conversation in a non-threatening way, it’s the difference between mentioning children as a part of your life and asking your date if they would like your children in their life. Reasonably speaking, it’s a date not a marriage proposal, treat it that way and it should be OK. Honestly, if you like the date, and they are the type that are scared off by children, its more than likely not going anywhere so go ahead and be honest.

I would insist that if you are not sure how you feel about your date or get any weird vibe from them, don’t bother discussing your children (and also sneak a text to a friend and have them call with a fake emergency). If you are not feeling it with the person don’t use your kids to try to scare them off, it’s unwise to use your kids as a pawn in a relationship either way. With that said, some dates are for fun only, for Mommy to be an adult and get out of the house. If there is a clear indication that you do not want any real relationship with this person and it isn’t going anywhere than I’m not sure you need to discuss your babies. Keep it light and for fun only if that is what you want.

Good luck with dating and with motherhood, sounds like you have the best of both worlds ☺

Q: I’ve realized I’m very attracted to younger men (I’m in my 50s). Do you know why that is? I’m worried I won’t be able to grow out of it and I’ll end up being unfulfilled. Any advice?

A: Hi Ms. Cougar, I am so glad to answer your question! Firstly, there may be many reasons why you are attracted to younger men, but I would not at all worry about it. As long as we are not talking about very young men, there is no clinical concern.

You may be curious about this trend in your taste and where it comes from, if that is the case Psychotherapy can be a very useful tool in helping you figure it out. I can throw out some common reasons why this may be the case but attraction is so personal and individual I am not sure it would help. What I can say is that younger men are typically less likely to commit in relationships, more energetic and possibly more affectionate. What’s unattractive about that?

Why do you need to “outgrow” your taste? Do you struggle to find dates with younger men? Maybe the key for you is to figure out what it is about younger men that you like, so that you are not unfulfilled. Take some time to think about what it is about younger guys that attracts you, and also when you noticed this trend. Has it been a trend throughout your life?

Sometimes when looking back we can see what has always been true for us, and sometimes your taste changes after a significant event in your life. I would also recommend that you pursue dating whoever it is you are attracted to. In general, men and women are often attracted to partners of varying ages for different reasons. So long as everyone is adult and consenting this is perfectly normal. You may be surprised to find out there are plenty of younger men who are attracted to women your age.

Hey, dating is hard no matter what! Don’t be so quick to judge yourself and don’t be so sure you will be unfulfilled ☺

Q: Hi there Shari, what are some of the best questions you can think of to ask on a first date? I’ve got one coming up soon! Thanks!

A: Shari’s top 5 best first date questions:

1. What should we do tonight?
I like phrasing the question that way because it sets the tone for the night. It eliminates this assumption that one person or another is in charge of the date, you are both going to have a say in it. If one person has made arrangements or plans for the date, they have an open door to let the other person know what they want to do. That person then has an idea of what they are in for and a right to agree or disagree. Either way, from the start the date is now a “we” and starts to shed away the anxiety.

2. How are you feeling today/night?
I like to remind people to always make an effort to show compassion and care. I wonder how many people forget to ask this of their date because they either forget how nice it is when someone asks (and then really listens to the response) or they are too anxious. It also may help you to know what is going on inside the mind of the person you are about to spend time with.

3. Where is your favorite place in this city/town/etc.?
Asking this question gives you a real good sense of where a person feels comfortable and can really open up a conversation. You may get stories about childhood or awesome nights out, maybe something even a little more emotional. This may prompt information about moves or relocations. Possibly some insight into a place you want to see or go to (date #2??).

4. So what’s it like to be you?
Sounds like a silly question but… can really get you some great information! In general, you are again showing care and concern for the person you are trying to get to know without demanding a serious or personal answer. This question can be answered in many different ways and gives a date the opportunity to let out what they feel is important or simply what they want you to know.

4.5 How do you feel about Obamacare? Just kidding, honestly just kidding don’t ask this on a first date ☺

5. How do you enjoy your down time?

Always a very informative, and relaxed question that evokes a good amount of information about a person. It’s cool to know what a person does when they have time to themselves, it may help you know how closely matched you are to this person in general. I always remind people that relationships at the core are not you on your dating behavior, it’s you when no one is watching. Anything you can do to get a sense of that person in a date early on will give you a heads up on whether this is for fun or for real.

Best dating advice I can give, HAVE FUN! There is nothing more attractive than someone enjoying themselves. There is no such thing as a bad date if you had fun, regardless of how it turns out.

Good Luck!

Shari Hardies, LCSW, is a social worker and contributor to Sono Bello Style, that has a true passion for improving the lives of others. She will be answering weekly user submitted questions on the topics of dating, relationships and live.

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