Major League Dating

Kimberly, 28
New York, NY

A few months ago I met a popular pro athlete at restaurant. Truthfully, I had no idea who he was, but my friend is totally into sports and wanted autographs for her brother and dad, so I accompanied her to his table.

Maybe it's because I didn't have the handicap being star struck, but I managed to strike up a pretty decent conversation with the guy and his friends. They were going out afterwards and invited us to go as well. I was a little hesitant because I didn't want to be the groupie who inadvertently ends up in a hotel room later that night, but my friend was not about to pass up the opportunity, so I went along to make sure she didn't end up to be that groupie.

It was a different club experience than any I've ever had in New York. It was kinda weird just walking up to the door of one of the hottest clubs and being shown inside and to your own private table with no questions asked. They were ordering $300 bottles like it was water!

To make a long story short, I ended up hitting it off really well with the athlete (let's call him "Joe") so we exchanged numbers. I took it, but I didn't plan to call him, it was a cell phone number, and I figured it was probably his personal assistant or somebody 3 degrees away from him so I probably couldn't reach him directly anyway. I really didn't expect him to call me either especially after I made it clear that I wasn't going home with him (not that he'd have had a problem getting someone to go home with him - there were women left and right just throwing themselves at him all night). He called me the next day (from the cell number he'd given me) and asked me out to dinner.

Since then, we've been dating regularly. It's kind of weird because he's travelling a lot and even when he's here, he's always so busy, and I'm used to being the top priority (or close to it) in my relationships. It's also strange when we go out seeing the reaction of women who will like flaunt themselves, even if he's holding my hand or something. I recently just slept with him after all these months, and now I'm feeling a little insecure. I mean, he has beauiful women throwing themselves at him all the time and he's in a lifestyle that I can't really afford so it's making me wonder why me of all the women he knows. He invited me to be his date for the ESPY Awards, but I didn't want to go. I'd feel so uncomfortable there with these women and dates wearing Prada and Gucci and Vera Wang, when I'd be in Bloomingdales. He was nice enough to buy me a dress to entice me into going, but that cost more than what I make in a month, so it was even more of a reason for me not to go.

My friends think I'm being stupid. They said should just enjoy it while it lasts and not to expect too much out of it, but I already like him a lot! I don't want to be just another groupie (although he's never made me feel like that). Should I have a talk with him and tell him how I feel, or should I just take my friends' advice and just have fun with it?

Well let me first applaud you! The fact that you could a) date someone in the public eye and b) fend off your insecurity for so many months deserves a round of applause. You're a better woman than I; I don't know if I could ever date a celebrity, pro athlete or any other person who constantly has attention on them, unless I knew them from before. Something about having to always jockey for time/attention from your significant other just doesn't appeal to me. And then there are the women; I'm not saying every pro athlete is a cheater, but when you have soooooo much temptation out there, I'm sure it's kinda hard not to cheat.

So you're kicking it (hope that's not a pun) with a pro athlete, huh? To be honest, when I read that, I was like, "Yeah, you and about 50 other women!" but I have to be fair; dude might actually be into you, for the same reasons you're so self-conscious about. One, you didn't know who he was, so you're not with him because of that. Two, you seem very conscious of/worried about the amount of money he spends on you - so you're not just a savvy gold digger who's looking for some material goodies. And three, he's probably used to getting into a chick's panties on the first date, and you didn't do that...

Point is, you have no reason to feel intimidated by his wealth and the women around him, especially since it sounds like he's making an effort to let you know you're special. I think most often than not, people in the public eye are more attuned to gold diggers and scam artists than us regular folk and can probably can spot one from a mile away. If he thought you were that type of girl, be sure he wouldn't have given you his (real) number on the first night! He's with you for a reason, so pop your collar and justify that reason instead of thinking that you don't deserve him...

But you can't be glib and go into this with rose-colored glasses either...I mean, don't expect to become Mrs. Joe anytime soon, and realize that with his type of money, he could easily be doing the same thing to other chicks in other states.

It's always best to be honest, in my opinion. That way, everything is out on the table, and you know exactly where you stand. You can't say, "Oh, I thought he knew that I felt this way!" and he can't say, "How was I supposed to know you felt this way?" Honesty gets everyone on the same page. So, tell dude how you feel about everything - his response will definitely let you know whether you're the side hussle or the main gig...But don't be too whine-y or too self-deprecating. A little insecurity is understable; total lack of self-esteem isn't...besides there's nothing more attractive on the opposite like well-worn confidence.

And next time missy, take the dress...if someone wants to do something nice for you, let them - it's not everyday someone will offer to buy you a nice dress or take you out to dinner. If things don't work out, you'll at least have some fond memories (and a fabulous dress!).

What do you think Kimberly should do? OR Email me your own dating question