Ask A Guy – Advice For A Lady Pimp

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We’re back with another Ask-A-Guy question and I’m happy about the change of pace the question presents. Check it out:

I am currently talking (just talking) to 5 guys. All of them are interested in me, I am really only interested in 2 of them. One of the guys I’m not so into wanted to be my boyfriend the second time we talked! It freaked me out, he had a “timeline” i.e. after we hand out 3 times we can be kissy in public, then after 6 times we will be bf/gf! The second guy quotes Dane Cook all the time and it annoys the crap out of me, and the third guy is 21 years old. I am 27 and don’t want to mess with the going out to the bars acting stupid all the time anymore.

1. Should I give all 5 of them a chance to take me out?

2. How do guys feel about a girl seeing more than one person at a time?

Lady Pimp

(Editor’s Note: I gave this reader the anonymous name “Lady Pimp”. She never referred to herself as such)

Well Lady Pimp,

Nice work! You’re out there looking good, doing your thing and getting attention because of it. Now, what to do with all this attention?!

Should you let all of them take you out a few times? Absolutely. There may be a side to one of them that wasn’t readily apparent at first. Spending a little time and listening to these guys will present a little more useful information. Maybe they have a passion or care deeply about something that you do as well. Ya know…don’t judge the book by the cover…and all that good stuff. Plus, we’re in a recession. There’s absolutely nothing wrong with 5 free meals/outings.

BUT

You should keep the fact that you’re surveying 5 guys at once to yourself. Don’t lie. Just say you are single, dating and enjoying meeting new people. We men have tricky egos. Some guys can handle the knowledge that you’re dating other men besides him with no problem. Others (most) would probably feel some kind of way about it. Maybe it would be a big deal to them, maybe it would be a small one — but it would be “a deal”. They would probably act a little different and if your goal is to get a real look at these guys — this is obviously counterproductive. Plus it’s disingenuous. Again, (most) guys act differently in a competition for your heart than they do once they have it.  If he thinks it’s a competition, you’re probably not going to get a genuine look at who he is.

Don’t string this along for too long, though. Giving 5 guys a tryout is one thing, but once it goes on for a while it becomes juggling. And 5 different guys are a lot of balls to keep in the air (he he he…sorry. I couldn’t resist). But seriously though, when you mess up while juggling you usually drop all of the objects — and one of those objects could be the guy you actually wanted…

I hope this was helpful. Now go forth bravely and pimp!

Peace, Love & Options Galore,

J (Pres)

Tagged as: Dating, Female, Pimp

Article by

Whassup people – my name is J.R. I’m a Jersey boy (born and raised), writer, people watcher and sports fan. I’m a black man with a degree, a job, no kids and no “priors”. It depresses me that those facts make me “rare”. I’m a guy’s guy. I’ve been in few committed relationships and a lot of…well…whatever you would call everything short of a committed relationship. I also have indisputable theories on life and love that you need to hear. Theories can be indisputable, right??

has written 27 article(s) for us.