[Httr12]

I am a young successful business owner on the fast track. I work 50 – 60 hours per week, which definitely cuts into my ability to meet new women and more importantly date. For about 2 months know I have been going to this bar which is attached to my office building. Now I know that many people will give me tons of crap for attempting to date a bartender but here it goes…

So I started asking her friends / coworkers about her situation. She kinda hooks up with somebody but they dont date. He too is an older bartender who is a likeable guy, but isnt going anywhere anytime soon and sees multiple women. They all wanted me to ask her out and take her on a date… so obviously I did! They definitely set me up really well and she said yes.

On our first date, I finished up my work day, changed out of my suit, and then picked her up at her house. I took her to a 5 star restaurant and had great conversation. Learned a lot about her family, life, and current situation. Some things stuck out in the conversation however. Her mother who cheated on her father for many years not just got divorced within the past several months. Obviously this makes for very poor timing on my part. And when I asked what she was looking for in terms of a relationship she said she didnt know. I smiled and said I was just wondering. The conversation quickly changed subject and everything was fun and easygoing.

So the date is not over yet. We are laughing and smiling and having an amazing meal! Afterwards I pay the bill and tell her we have one more stop. I end up taking her to the gun range and she loves it. She once worked for a police force and knew how to handle a gun quite well (once again, very sexy in my book ha). During this part of the date, we are both giving googly eyes and there is a serious connection going on. No I am not overlooking this, part of my job is to read people. However I definitely realize that there are some trust issues and likely bad timing on my part in terms of her current family situation.

After we finish, I drive her home. Its a long 45 minutes back and we talk and laugh and make fun of eachother. She claims she is better than me at shooting (totally not true, I let her win). I pull up to her home and tell her I had a great time and that we should do it agian. She reaches over, and gives me a hug and tells me goodnight. Now this doesnt bother me at all, I am completely fine with things going slow. Slow and steady wins the race!

3 Days later its my birthday! My friends take me out for drinks and at the end of the night we visit her at the bar she works at. She is happy to see me and spends a few minutes in between serving people to small talk with me. I leave and tell her goodnight.

Here is where I get confused. Originally we texted and chatted all the time and then complete silence. So I wait a week and visit her at the bar again. Play it cool, dont come off as desperate, and we share a few words here and there together. I then text her the next day to ask if she would like to go to a football game with me becuase I had extra tickets. She says she is really busy and can’t. I am a very direct and forward person, so I tell her if she isnt interested then let me know so I dont waste my time or hers. I realize this is not the most sensitive way of conveying this message, but its who I am. If somebody means something to you, you will make the time happen. She replies back with this:

“No no I really had a great time wth you the other night, it was a lot of fun. But Im not jumping out of my seat to go out again and that tells me something.Youre a great guy and we are very different people, and you’re right I dont want to waste anyones time”

Now I get rejected every day in the business world. Heck thats what the most successful people experience, every no is one step closer to a yes. But this is different. I dont fall for girls over crushes or on first dates. But this is the most beautiful, amazing, and cool girl I have ever met in my life from a 10,000 foot introduction. Therefore I will not walk away that quickly. I really felt a strong connection in our time together and I think she did too. I wont let this one go without a fight, however I am willing to wait to let the dust settle. My thought process is to play it cool and maybe try to become friends with her and hang out platonically in hopes that it may blossom to someting more. Normally I would move on and forget about it but I just cant, call me crazy haha. So my question is this:

1.) Is it dead completely, or maybe can I try a different route in the future with her
2.) What does that message really mean. Do you think it is a complete waste of time for me to even try?

Thank you and I hope your feedback will help me jumpstart this dead end situation.

[Danneskjold]

Heck, I’m no expert, but I think the message you sent after she told you that she couldn’t make the football game was bit brutal.

If you really feel you guys made a connection on that date, then I would try to see her again; If you can get a quiet 2 minutes with her in the bar, in a corner, or if not, ask her out for a coffee. Either way, make it obvious (without actually saying it!) that you only want 3 minutes of her time. Then apologise for that message, say you felt bad about it, and you would really like for her to consider going out again for a meal. Ask her to text or call you when she’s got time, and then leave the ball in her court. Wait for her to call. But you’d better make that apology a good one, and be sincere about it.

Remember, people always remember how you make them [i]feel[/i], not necessarily the things you do or say. Ya gotta make her feel [i]good[/i] about herself, and about you.

Good luck!

[Httr12]

You are definitely right. I came off like a big asshole there, certainly wasn’t the intention. Thank you for the wisdom!

[April Masini, your AskApril]

My advice is to pursue her, but quit texting and giving ultimatums. This isn’t a client you’re trying to win. It’s a woman. 😉 Flowers, chocolates, poems — you know what I’m talking about. Old fashioned courting has a place in today’s world. You need to show her you’re chasing her, and give it your best shot. She’s not jumping out of her seat to date you again, so you have to bring a better A game. Telling her you had extra tickets to a football game is different than asking her if she’d like to go to something you arranged specifically for her.

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[Httr12]

April you are brilliant. Thank you for yoir help!

[April Masini, your AskApril]

You’re very welcome! 😀

[Httr12]

Do you think I should approach the situation with an apology first?

[April Masini, your AskApril]

No. Don’t call attention to faux pas’. Instead, just pursue by doing the right thing. 🙂

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