Inexperienced & a Date w/ an Older Guy

iVillage Member
Registered: 06-26-2004
Inexperienced & a Date w/ an Older Guy
2
Tue, 12-07-2004 - 3:31am

How honest should I be with my past 'inexperience' when it comes to dating?

Here's the dilemma- there has been an "older" guy that's interested in me. I've had a feeling that he's liked me for awhile now- he would come fairly regularly into where I work and he always stopped to talk to me. He asked me to a concert one night about 3 months ago, but I had to decline his offer due to plans I already had for the evening.

But his awesome sense of humor and gorgeous blue eyes definitely caught my attention.

As time went on it became a bit hit or miss. I didn't see him often, and the only time I saw him was at work- and unfortunately, I was usually pretty busy whenever he came in.

However, about four weeks ago I had the chance to talk to him more in depth. He came in after being absent for awhile. When I smiled and asked, "How are you? Where have you been??" he looked me in the eye and answered, "It's cold outside, I'm miserable, I've been sick, and my girlfriend and I just broke up."

I was pretty shocked at his honesty, as we hadn't previously talked for more than 5 or 10 mintues at a time. The rest of the conversation that day went really well- I didn't ask him about the breakup, but we talked about other stuff. It turned out we have a lot of similar interests. He wanted me to listen to a certain band off the internet, but I mentioned briefly that my computer was broken. He showed up two days later and surprised me with a burned CD of that band.

The next week after I managed to catch him at work again when I wasn't busy, and he mentioned he was traveling over Thanksgiving. I said, "I'm so jealous, I'm stuck here..."

He answered, "That's why you need to come with me." He wasn't laughing or joking. He was being dead serious.

Heh, as you can see, he obviously has no problems communicating exactly what he's thinking.

The Friday after Thanksgiving I was at work again and he called me- at work! He was still out of town and calling me from his hotel. It *completely* threw me by surprise. He said he just wanted to make sure I had a good Thanksgiving, as I sounded kind of bummed about my Thanksgiving plans. We chatted for about 10 more minutes and hung up.

The next week I talked to him and begged him to bring in pictures from his trip. He did one night and let me look at them. He said, "I'm going back there in a few months, you need to go with me."

And then he said, "I was thinking I need to do some Christmas shopping...you should come with me..."

I said that I'd love to, but I work strange hours and don't have the typical Saturday-Sundays off that most people do. He said, "Okay, I'll just take a day off of work."

I saw him the next day and he said, "Next week Thursday- we're going, I took it off."

Yowza. He took a day off from work to spend it with ME. Everything looks like it's going well, right?

In all honesty, I am feeling EXTREMELY nervous right now. He is older than me by five years- and while that doesn't seem like it's a huge deal, it is to me because I don't have a whole lot of dating experience. Make that almost NO dating experience. And no sexual experience- I'm still the big v-word. :P

I'm in my early 20's, and I was an ugly duckling in elementary school through highschool. Even though it wasn't that long ago, I have changed *a lot* physically since that time in my life. I don't mean this to sound petty or vain- but I am considered to be really attractive now. People, even strangers now compliment and praise me all of the time on my looks, and it's so hard because I'm still not fully used to it. I almost feel like it's a bit of a facade. While I no longer feel ugly (inside or outside!), I still feel very nervous and awkward. I have had *a lot* of guys "persue" me over the past two years and due to this insecurity of having no dating experience, I have avoided most of their advances.

However, I've realized that the only way to GET dating experience is to actually date. Duh. Which is what I want to do.

Which brings me back around to this current guy. Even though there is only a 5 year difference between us, I'm in my early 20's and he's in his late 20's. When we talk, it doesn't seem like there is that huge age gap between us at ALL.

In fact, when he first told me his age I was completely shocked! I think we're on an even keel with our interests and situations in life- both of us are working full time, living on our own, and independent. I also am guessing (hoping!) that he's passed the "playa/partying" stage of life and is ready to settle down. But I also know that he's very good looking and could have almost any girl that he wants.

And I'm not a "typical" girl that gets giggly/ditzy around guys. I believe a lot of people expect me to be that way because of the way I look, but it's just not me. I don't like clubbing, I don't like bar hopping. I spent the first 20 years of my life having "Intelligence matters, not looks!" drilled into me because I was so 'ugly' at that time, and I still definitely go more for intellectual stimulation. ;)

How honest should I be with my past relationship experience? How soon do I tell him? What is the best way to tell him this without sounding like a complete goon? And does anyone else have any other tips/advice to give me? Thank you so much! :D

iVillage Member
Registered: 03-26-2003
Tue, 12-07-2004 - 2:04pm

sillygirlie12...

Why call attention to the negatives (aka your 'inexperience when it comes to dating')? Pianoguy thinks you should ACCENTUATE THE POSITIVE instead. In other words, enjoy your time with this gentleman (on Thursday)...and keep the conversation light. Christmas is a perfect time of year to share your thoughts about lights, food, decorations, presents, religion and basically everything else connected with it. Hopefully, this man will do the same?

However...

If he gets a little carried away and wants to 'push himself on you'---PULL BACK and nicely explain to him that "it's much too early in our relationship to get serious. So let's just enjoy the moment together as 2 good friends!"

Pianoguy

iVillage Member
Registered: 11-10-2004
Tue, 12-07-2004 - 8:22pm
Cheers Sillygirlie,
Bellina here! It sounds to me like he's very nice,interested and smitten,despite being
a trifle older! Just enjoy the way you're both seeing each other for present time.I believe he's mature enough to not push you into more intimacy,be friends first.Then when
down the road,with more dates and really getting to know his interests,life goals,family/friends and the timing seems right,express yourself then.If he's sincere in his feelings this will not matter,dear your still very young.Enjoy the nice connection you both feel for each other,and if he's meant to be a serious love potential this will happen.Meanwhile do somemore mutually enjoyable things like Christmas shopping,viewing town decorations,local musical holiday events..all lighthearted pleasures..Be happy and best wishes...Bellina