I'm a 40 something male attorney to a "top 25" local law school, which seems like a silly thing to say, but I mention it only to let you know that I may have some similarities with your date.

I just wanted to tell you that I think it's cool that you're putting yourself out there. I think it might help you to relax and have a good time if you try to keep in mind that the stakes aren't really that high. Try to have a good time, and the rest will take care of itself. If not, then it wasn't meant to be with this guy, and there will plenty of others.

If you're searching for something to talk about, you could talk about why you wanted to go to this particular restaurant and what is it about it that interests you. And then how the experience related to your expectations.

And remember, everyone likes it when you laugh at their jokes. Have fun.

One tip, don't waste your witty banter or fun facts about yourself via email leading up to the date. Save that stuff for the actual date. I did a lot of online dating and kept it down to two email exchanges tops if possible (one "hi I saw your profile-insert something witty in response and two "want to meet for coffee or a drink"). Last piece of advice, dating is like a lot of things. You get better with practice. I am now married to someone I met on chemistry.com
Don't put so much pressure on yourself OP. Look it could suck but if you internalize that and think its all because you can't make small talk you are gonna burn out before you even catch fire!

Anonymous wrote:

Anonymous wrote:He's an attorney and went to a top 20 law school. He's local to the area and loves sports, like me. We're going to an Asian restaurant that I've been wanting to try for sometime. I'm just a little intimidated because more accomplished than I. Although I have a degree, I've been stagnant in my career since relocating

M attorney here. Ask him about his area of practice, why he chose it, does he like it, his clients, any big cases/deals/projects, his firm, his coworkers, does he travel for work, etc. That's two hours right there

Ha! Just remember-it's a date, not an informational interview!

Anonymous wrote:He's an attorney and went to a top 20 law school. He's local to the area and loves sports, like me. We're going to an Asian restaurant that I've been wanting to try for sometime. I'm just a little intimidated because more accomplished than I. Although I have a degree, I've been stagnant in my career since relocating

M attorney here. Ask him about his area of practice, why he chose it, does he like it, his clients, any big cases/deals/projects, his firm, his coworkers, does he travel for work, etc. That's two hours right there

He's an attorney and went to a top 20 law school. He's local to the area and loves sports, like me. We're going to an Asian restaurant that I've been wanting to try for sometime. I'm just a little intimidated because more accomplished than I. Although I have a degree, I've been stagnant in my career since relocating

Agree that you shouldn't get into relationship history on a first date, but politics is fine. What info have you gleaned from his profile? If you have mutual interests, have some shared topics to bring up. If he has interests you don't know anything about, ask him about them. If you are meeting at a bar/restaurant/coffee shop then ask him about other places he likes/has been to recently. And congratulations! Even if it isn't the best date of your life, you are doing it and it will get easier over time.

Go read Date Lab in The Washington Post for the past few weeks, you may get topic ideas from there.

Don't talk about lack of relationships either. Guys like a sweet, charming woman. If you have a hook (interesting hobby, from an interesting state, etc.) work that in.

Avoid discussing politics, and prior relationships.

MikeL wrote:Ask him about his job, family, education, hobbies, etc.
Volunteer your story about the same things without interrupting or seeming to "one up" him.
Be relaxed, smile, have a good time.

dont do that - way too many people in this town do that.

Do ask about his interests, anything cool he has read, where has he traveled recently, etc.

Don't talk about your exes.

Honestly be your urself. Conversation can flow frok anything. Foods you like, restaurant faves, how your respective summers went how dating online has been etc. I say relax. Be excited and let the conversations flow naturally.

I have a hard time getting the conversation to flow with most people, so I know what you mean.

For me, conversation is easier when we share an experience or interests. So instead of going straight to dinner, which is very much about how good of a conversationalist you are, maybe you could see an interesting play, concert or whatever floats your boat as something to break the ice? Or to just walk around the city or park, which will naturally give you stuff to discuss about the world around you, instead of personal stuff all the time.

Can you spend the date in a place that is familiar and comfortable for you?

Ask him about his job, family, education, hobbies, etc.
Volunteer your story about the same things without interrupting or seeming to "one up" him.
Be relaxed, smile, have a good time.

Go ahead and poke fun at me now. I'm a 30 year old woman with a huge lack of experience in the relationship arena. I decided to sign up for online dating and I'm going out to dinner this week. I'm a bit nervous as I am socially awkward and I am interested in him a lot. I really can't allow my awkwardness to screw this up. We've talked about career aspirations and related information. I definitely want to deviate from that. Please help!