Finishing up a divorce 
I’m at some point going to date again. Right now, I think that point is at least 6 months away. I want to use that time constructively, so I want to devise a dating bootcamp™!
I want to brush up on my skills, learn the (new) rules, improve my odds.
First thing is easy: hitting the gym to get back to dating weight.
the rest, not so easy, so I need suggestions.
I’m a mid-thirties male. Target will be early to mid-thirties females.
I’m in sales, and can hold a conversation, but I’m shy, and never really start a conversation. The last time I wentr out with anyone other than my (soon to be ex)-wife is at least 13 years ago…
Suggestions?
First of all, sorry to hear about your divorce. Don’t complain to any of your gay friends about it, though, seems everyone’s real touchy for some reason lately.
My advice is to join as many social groups as your schedule permits, and then create outside activities and involve people from these groups. For example, if you’re in a play or a musical (local theatre can be lots of fun), offer to take a few of your friends in the cast out to dinner and a movie, or invite them over to your house to watch something rented. Maybe go see a concert or a political debate. If you’re in a model rocketry club, maybe go to an air show… or dinner and a movie, or a local theatre show! Cross-pollinate your groups of friends. Let them all know that you’re “on the market” and they will soon fall all over themselves to find you prospects. At the same time, you’re having fun experiences and meeting people, all of which are great fodder for a date. The more you talk about “how much fun” X or Y was, and the less you complain on a date, the more likely she is to think that you–by association–are fun.
When you say “sales” I assume that means a bit of traveling is required, which I think can be a good thing. Lots of online communities (some possibly related to your hobbies!) have get-togethers, gatherings, parties, or what-have-you. This means that, if you’re a member in good standing of a few social groups and also maybe one or two websites with a broad readership, you can manage to go see some far-flung internet friends when you’re on travel. A good example: when I was in LA a few weeks ago, I had dinner with a high school friend one night, an internet pal the next, and some project engineers on my team the third night. By the third night, I had cool stories to tell about obscure restaurants in the area, whereas the locals on the team were recommending places like The Olive Garden. I would argue that having a varied social network made me the more interesting person to dine with that evening.
Now that you’ve got a few circles of friends, hopefully you have some pals who are couples. If you’re comfortable going out with these folks, then ask if they’d mind a double-date once you’ve picked a special lady. You ask her: “Hey, some friends and I are going to go see 50 First Dates on Friday and I thought it’d be really fun if you would come with us.” Your helpful couple friends should be willing to give you a hand; to them you say “I’d like it if you’d help me keep my first date with this lady from being awkward.” Suggest to your lady friend that if she has a good time, she could introduce you to some of her friends, too. A much better way to break the ice would be to hang out with her socially; invite her to one of your groups that you think she might enjoy, or to one of the side excursions (unrelated to the hobby) if she’s not interested in that hobby. At a minimum have one other couple along. At a maximum, a group of seven or eight.
By avoiding the one-on-one “first date” you can also avoid awkward silences and the conversation-killing “so tell me about yourself” type lines.
Disclaimer: the last time I dated was six years ago. Since then I’ve been dating the same girl, who is now my fiancée.
Hey Iso - we met up at North Park. I’d not seen you posting recently, I was curious as to how you were doing.
Since you’re in sales, you can look at starting up a conversation with someone the same way you do as making a sale. You’re playing a role when you’re a salesman. You’re Iso, the sales guy, so it’s ok to just pop over and talk to someone and say “Hi, would you like to buy this?”
When striking up a conversation with someone, take up that role or some role that lets you do so. You don’t have to start the conversation as Iso, cause, you know, you’re shy. Start it up as Sales-Guy Iso, think of yourself as being someone else, so it’s not as personal if you get shot down. If you do start talking, then you can switch to normal Iso, now that you’ve broken the ice.
Every few weeks, I head out to the local contra dance on friday nights. The next one I’m definitely going to is at the end of march. If you want to go but think you’ll be out of place, give me an email - I’ll meet up with you there, show you the ropes.
Just make sure that when you’re picking up chicks, you’re drinking. Girls love guys with accents and yours gets thicker and thicker the more you drink.
I am also a divorced male. My advice…be yourself. Unless you are a real asshole, in which case you should pattern your behaviour after a friend who is a good person. You are from my neck of the woods. Ever been to Moondog’s in Blawnox? Good, low key place with live music.
Married girl here…single 'til 36 though! (am 42 now) Tips from the other side: don’t whine about your ex; don’t make first date somewhere you absolutely HAVE to make conversation - as a girl who’s not terribly good at it - and your shyness - could be conversation stall…somewhere like a live local band; movies are a bit too conversation killing.
Personal notes from my own: set the time and be on time; smell nice (sorry, that’s a very personal one but one of the points that got my now hubby a second date); dress well; be a gentleman; let us know what we should wear: dress, jeans, etc.
P.S. Don’t dismiss older women - you just never know!! 