Matchmaking. Kind-of.

After being unlucky in love for some time, I've recently changed jobs, and several coworkers are trying to set me up with not one but two eligible male employees. I work in the kind of setting where dating among coworkers is not frowned upon, and I find both to be intriguing guys, so I'm interested. The only problem is my friends playing matchmaker don't seem to have put much effort in beyond, "I think you should date so-and-so," and I'm not sure if the attraction is mutual with either candidate. Is there a way I can subtly move things along without seeming overbearing? Considering it was both of my coworkers' ideas and not mine (if anything, dating has been pretty far from my mind recently), I don't feel like I'm in much a position to do anything here.

Uncertain

It sounds like your coworkers aren’t playing matchmaker so much as they’re making semi-informed suggestions about other single people they know. Which is fine, but, as you point out, doesn’t really move things along for you.

It also sounds like you’re interested but not completely bowled over by either of these potential dates. This is also fine but takes some urgency out of the situation. Since you’re not really interested in pursuing either of these guys full-tilt and you all work together and you’re interested in dating either or both of them, I advise slow-playing it a little bit and letting him/them come to you.

The next time your friends bring up the idea of your dating one of these guys (or, if you don’t want to wait, the next time you gently steer the conversation in that direction), dig a little bit. Ask if your friends are sure he’s single, if they know him well, why they think you should date him, etc. Dig enough that they know you’re a little bit interested. Sometimes that’s all it takes to get things going. They mention something to another mutual friend or to the guy himself, he knows you’re a little bit interested and then things start to happen.

I suspect the wheels are already in motion. If you all work together and people are making suggestions to you, (the same or other) people are probably making the same suggestions to the guys in question. And/or the same idea has likely occurred to the guys themselves.

A Friend of a Friend of a Friend

About a month ago, I traveled to Oregon to visit a friend (and her husband and their baby). While I was there, we went to a party at the home of one of my friend’s husband’s friends. The host also had an out-of-town friend visiting (from Vancouver). I’ll call the Vancouver guy Sam. Well, Sam and I kind of hit it off at the party. We flirted, laughed a lot, seemed to have a lot in common and there was definitely a physical attraction. But, since we were both visiting other people, we didn’t really have the opportunity to spend much time together beyond that one party (where we did spend basically the entire time together, almost to the point of being rude to our other friends). We all got together one other time during the week that I was there, but Sam and I didn’t get to spend any time one-on-one, and the awkwardness of barely knowing (but liking) each other in front of all our mutual friends didn’t help anything.   

Sam and I ended up kissing once, and we talked about him coming to see me or vice-versa. We’ve been apart about four weeks, and we’re still texting a lot and emailing some. My question: Is it even worth it for me to make plans to see him or for him to come here? I really enjoyed him and am still excited to be talking to him, but I don’t see where this could go. Even if we do get along great in person, we live on opposite coasts. I’m a little reluctant to get pulled into a long-distance relationship. I kind of feel like I should write this off to vacation fun and get on with my life here. Don’t you think?

Wavering

Whaaaat?? Write off someone you met and liked who also seemed to like you? Someone who lives in an awesome city and is inviting you to visit? Someone you know is probably not a killer because he’s been vetted by a friend of a friend of a friend? Why would you do that?

If your life here is full and complete and you’re not interested in dating, then yes, write this guy off. If the perspective of a few weeks has helped you see he wasn’t so right for you, then yes, write him off. But I don’t get either of those things from your letter. It sounds like you liked him and are curious to get to know him a little more. Ask your friend to ask her husband to ask his friend about Sam. To make sure he’s not in a relationship and not a serial killer. If those tests come back negative, I say plan a trip. (A kind of short one—three or four days.) Either there or here, whichever you prefer. Traveling there sounds like fun and showing him around here would also be fun.

Once you spend some time together, you’ll know more clearly whether you want to pursue things with him. If you don’t, no problem, he’s a continent away. If you do, you can take things as they come and see how the distance works out.

Give Me My Money Back

A reader sent this in after seeing the column about taking a landlord to small-claims court.

Just a note about security deposits: If the court finds that you are entitled to a return of your security deposit, then you are also entitled to court costs (and attorney's fees). Depending on how many units the landlord has (or whether there is a management company, among other factors), you may also be entitled to treble (3x) your security deposit as damages.

Thanks for the info. Three times the security deposit is almost enough to make you hope your landlord holds out on you.