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You’ve got questions? He’s got answers! Need advice?

Send your questions to Terrance:

Dear Gay Best Friend,

I’ve been talking to this girl for over a month now. We meet online and had, and, still do have great conversation. We have been out three times in this time period, but haven’t been out for about three weeks. I haven’t even seen her during this time.

She’s a single mother of a 5-year old and always says it depends on if she can get a babysitter. Her mom or sister is the only ones who she will let watch her daughter. I know that being a single mother is hard and it takes a lot out of her. But, at the same time, it’s always me doing all the calling, the texting, the trying to set up dates and mostly getting shutdown. She said that she believes that it’s the guy’s job to do all the setting up and communication when they are just dating.

I’ve even offered to take her and her daughter out for some mini-golfing, a circus, etc. The times we have hung out we have had great chemistry and things always go good and we really get along well. She says she is interested in me and wants to see what can come of it. Our obstacle is how to get to that point when we can spend time together. So, my question is am I going up against a no-win battle, or should I still show interest but just back up a little bit? I really need some advice about this right now, because I do like her. – Really Into Her

“My Wife’s Job Fired Her and I Think It’s Because Of Her Health”

Dear Really Into Her,

WOW! I’m impressed by your letter. You’re a stand-up guy who is willing to put in some time and effort into a single mother, and even trying to get to know her daughter. That is commendable if I must say so myself.

But, I think there are several issues that may be lurking and you may not be aware of them. Now, I totally understand her only wanting to leave her daughter with her mom and sister because she doesn’t trust her daughter with strangers. And, it is difficult raising a 5-year old child alone. I am assuming her daughter may be in school, and there are lots of things she has to do with her child such as getting her ready for school during the week, and keeping her on a routine. Bedtime is one of them. That’s one thing you should know about raising a child. You have to keep them on a routine and schedule. So, she may not have the time to get together with you during the weekdays. And, I know her weekends are probably tied up with her daughter and other household chores. So, it is pretty difficult for her to go out.

And, I totally agree with her that it is the man’s job to call and show his interest in a woman. It’s called courting. And, in a previous letter, where I gave advice, I explained that courting is taking the time to get to know one another. The guy is calling, engaging the conversation, inviting the woman out on dates, sending cards and flowers, and being creative in the dating process. She wants to know you are going to put in work because she’s probably been down that road and may have some regrets. Which leads me to why she may have a wall up and won’t let you get close. I am sure she is dealing with her child’s father and it may not be all cozy and good. There could be some emotional and mental damage from her previous relationship which is preventing her in letting you get close to her and her daughter. You are going to have to earn her trust and it may take a little more work and time.

Or, she may be confused and her child’s father may still be in the picture. Even though she spends time with you and she enjoys your company, her child’s father is the one she will forever be tied to. And, she may not be emotionally equipped to handle that and could be thinking perhaps it would be better to have the father of her child in her life instead of a new man.

But, you know how to get to the bottom of all of this and stop speculating and trying to figure out what to do? Ask her. Ask her the straight up truth about what’s going on. Ask her if the child’s father is still in their lives and in what capacity? Ask her if she’s been hurt in the past. It’s very important that you two start a line of communication and one in which she feels comfortable sharing with you. And, let her know how much you like her and that you plan to stick around. Express to her how you would really like to get to know her daughter in the process. I suggest that you see if she is open to an evening at their home where you guys order pizza, and watch some kid’s movies. Yes, my brother, you are going to have to put in work with her. You are really going to have to be very creative in your dating suggestions and the circus and mini-golf were great, because they included her daughter. I say the next time Elmo, or one of those Disney shows are in town, you invite them. Even check out the weekend metro section of your paper and see what child events are happening such as readings at the library, or even a hay ride, it is the fall, and the holidays are coming. Even check out Chuck E. Cheese, and Gymboree in your area. It’s a great child activity. There are lots of great activities which includes young kids. And, once she sees that you’re for real and on the up and up, she will begin to let that wall down and allow you into her life. So, don’t give up just yet. Don’t throw in the towel. It’s like the saying that goes, “Don’t give up before the blessing. It may be right around the corner.” – Straight From Your Gay Best Friend

Make sure to get your copy of my new book, STRAIGHT FROM YOUR GAY BEST FRIEND – The Straight Up Truth About Relationships, Work, and Having A Fabulous Life (Agate/Bolden – October 2010; $15). It is available in bookstores everywhere, and on Amazon, HERE!

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